Pesticidal compositions and related methods

ABSTRACT

A pesticidal composition comprises a pyridine triazole compound of formula I or any agriculturally acceptable salt thereof, wherein R 1 , R 2 , R 3 , R 4 , R 5 , Z, and x are as described herein. A method of controlling pests comprises applying the pesticidal composition near a population of pests.

CROSS REFERENCE TO RELATED APPLICATION

This application claims the benefit of U.S. Provisional PatentApplication Ser. No. 61/894,348, filed Oct. 22, 2013, the disclosure ofwhich is hereby incorporated herein in its entirety by this reference.

TECHNICAL FIELD

This disclosure relates to the field of compounds having pesticidalutility against pests in Phyla Nematoda, Arthropoda, and/or Mollusca,processes to produce such compounds and intermediates used in suchprocesses. These compounds may be used, for example, as nematicides,acaricides, insecticides, miticides, and/or molluscicides.

BACKGROUND

Controlling pest populations is essential to human health, modernagriculture, food storage, and hygiene. There are more than ten thousandspecies of pests that cause losses in agriculture and the world-wideagricultural losses amount to billions of U.S. dollars each year.Accordingly, there exists a continuous need for new pesticides and formethods of producing and using such pesticides.

DISCLOSURE

Definitions

The examples given in the definitions are non-exhaustive and must not beconstrued as limiting the present disclosure. It is understood that asubstituent should comply with chemical bonding rules and stericcompatibility constraints in relation to the particular molecule towhich it is attached.

“Alkyl” means and includes an acyclic, saturated, branched or unbranchedhydrocarbon. Non-limiting examples may include methyl, ethyl, propyl,isopropyl, 1-butyl, 2-butyl, isobutyl, tert-butyl, pentyl,2-methylbutyl, 1,1-dimethylpropyl, hexyl, heptyl, octyl, nonyl, ordecyl.

“Cycloalkyl” means and includes a monocyclic or polycyclic saturatedhydrocarbon. Non-limiting examples may include cyclopropyl, cyclobutyl,cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclodecyl, norbornyl,bicycle[2.2.2]octyl, or decahydronapthyl.

“Alkenyl” means and includes an acyclic, branched or unbranchedhydrocarbon containing at least one carbon-carbon double bond.Non-limiting examples may include ethenyl, propenyl, butenyl, pentenyl,hexenyl, heptenyl, octenyl, nonenyl, or decenyl.

“Cycloalkenyl” means and includes a monocyclic or polycyclic hydrocarboncontaining at least one carbon-carbon double bond. Non-limiting examplesmay include cyclopentenyl, cyclohexenyl, cycloheptenyl, cyclooctenyl, orcyclodecenyl.

“Alkynyl” means and includes acyclic, branched or unbranched hydrocarboncontaining at least one carbon-carbon triple bond. Non-limiting examplesmay include ethynyl, propargyl, butynyl, pentynyl, hexynyl, heptynyl,octynyl, nonynyl, or decynyl.

“Cycloalkynyl” means and includes a monocyclic or polycyclic hydrocarboncontaining at least one carbon-carbon triple bond. Non-limiting examplesmay include cycloheptynyl, cyclooctynyl, or cyclodecynyl.

“Aryl” means and includes an aromatic compound with or without anysubstitution. Non-limiting examples may include phenyl or naphthyl.

“Alkoxy” means and includes an alkyl group containing at least onecarbon-oxygen single bond. Non-limiting examples may include methoxy,ethoxy, propoxy, butoxy, cyclopropoxy, cyclobutoxy, or cyclopentoxy.

“Alkenyloxy” means and includes an alkenyl containing at least onecarbon-oxygen single bond. Non-limiting examples may include allyloxy,butenyloxy, pentenyloxy, hexenyloxy, heptenyloxy, octenyloxy,nonenyloxy, or decenyloxy

“Alkynyloxy” means and includes an alkynyl containing at least onecarbon-oxygen single bond. Non-limiting examples may includepentynyloxy, hexynyloxy, heptynyloxy, octynyloxy, nonynyloxy, ordecynyloxy.

“Cycloalkoxy” means and includes a cycloalkyl containing at least onecarbon-oxygen single bond. Non-limiting examples may includecyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy,cycloheptyloxy, cyclooctyloxy, cyclodecyloxy, norbornyloxy, orbicyclo[2.2.2]octyloxy.

“Cyclohaloalkyl” means and includes a monocyclic or polycyclic,saturated substituent comprising carbon, halogen, and hydrogen.Non-limiting examples may include 1-chlorocyclopropyl,1-chlorocyclobutyl, or 1-dichlorocyclopentyl.

“Cycloalkenyloxy” means and include a cycloalkenyl further consisting ofa carbon-oxygen single bond. Non-limiting examples may includecyclobutenyloxy, cyclopentenyloxy, cyclohexenyloxy, cycloheptenyloxy,cyclooctenyloxy, cyclodecenyloxy, norbornenyloxy, orbicyclo[2.2.2]octenyloxy.

“Alkylthio” means and includes an alkyl group containing at least onecarbon-sulfur single bond.

“Haloalkylthio” means and includes an alkyl group containing at leastone carbon-sulfur single bond and halogen atom.

“Halo” or “halogen” means and includes fluorine, chlorine, bromine, oriodine.

“Haloalkyl” means and includes an alkyl group substituted with at leastone halogen atom.

“Haloalkoxy” means and includes an alkoxy group substituted with atleast one halogen atom.

“Heteroatom” means and includes sulfur (S), oxygen (O), or nitrogen (N)atom.

“Heteroalkyl” means and includes an alkyl containing at least one sulfur(S), oxygen (O), or nitrogen (N) atom.

“Heterocyclyl” means a cyclic substituent that may be fully saturated,partially unsaturated, or fully unsaturated, where the cyclic structurecontains at least one carbon and at least one heteroatom, where saidheteroatom is nitrogen, sulfur, or oxygen. In the case of sulfur, thatatom can be in other oxidation states such as a sulfoxide and sulfone.Examples of aromatic heterocyclyls include, but are not limited to,benzofuranyl, benzoisothiazolyl, benzoisoxazolyl, benzoxazolyl,benzothienyl, benzothiazolyl, cinnolinyl, furanyl, imidazolyl,indazolyl, indolyl, isoindolyl, isoquinolinyl, isothiazolyl, isoxazolyl,oxadiazolyl, oxazolinyl, oxazolyl, phthalazinyl, pyrazinyl, pyrazolinyl,pyrazolyl, pyridazinyl, pyridyl, pyrimidinyl, pyrrolyl, quinazolinyl,quinolinyl, quinoxalinyl, tetrazolyl, thiazolinyl, thiazolyl, thienyl,triazinyl, and triazolyl. Examples of fully saturated heterocyclylsinclude, but are not limited to, piperazinyl, piperidinyl, morpholinyl,pyrrolidinyl, oxetanyl, tetrahydrofuranyl, tetrahydrothienyl andtetrahydropyranyl. Examples of partially unsaturated heterocyclylsinclude, but are not limited to, 1,2,3,4-tetrahydroquinolinyl,4,5-dihydro-oxazolyl, 4,5-dihydro-1H-pyrazolyl, 4,5-dihydro-isoxazolyl,and 2,3-dihydro-[1,3,4]-oxadiazolyl. Additional examples include thefollowing:

“Pesticidally effective amount” means and includes an amount of activematerial that causes an adverse effect to the at least one insect,wherein the adverse effect may include deviations from naturaldevelopment, killing, regulation, or the like.

“Control” or grammatical variations thereof means and includesregulating the number of living insects or regulating the number ofviable eggs of the insects.

“Synergistic effect” or grammatical variations thereof means andincludes a cooperative action encountered in a combination of two ormore active agents in which the combined activity of the two or moreactive agents exceeds the sum of the activity of each active agentalone.

Pesticidal Compounds

In one particular embodiment, a pesticidal composition comprises apyridine triazole compounds of formula I, or any agriculturallyacceptable salt thereof:

wherein:

R₁, R₂, and R₄ are independently selected from hydrogen, F, Cl, Br, I,substituted or unsubstituted C₁-C₆ alkyl, or substituted orunsubstituted C₁-C₆ haloalkyl, wherein each R₁, R₂, and R₄, whensubstituted, has one or more substituents selected from F, Cl, Br, I,CN, NO₂, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₁-C₆ haloalkyl, C₃-C₁₀ cycloalkyl,or C₃-C₁₀ halocycloalkyl where each of which may be unsubstituted orsubstituted with R₁₁;

R₃ is selected from hydrogen, F, Cl, Br, I, CN, NO₂, substituted orunsubstituted C₁-C₆ alkyl, substituted or unsubstituted C₂-C₆ alkenyl,substituted or unsubstituted C₁-C₆ alkoxy, substituted or unsubstitutedC₃-C₁₀ cycloalkyl, substituted or unsubstituted C₁-C₆ haloalkyl,substituted or unsubstituted C₆-C₂₀ aryl, substituted or unsubstitutedC₁-C₂₀ heterocyclyl, OR₁₁, C(═X₁)R₁₁, C(═X₁)OR₁₁, C(═X₁)N(R₁₁)₂,N(R₁₁)₂, N(R₁₁)C(═X₁)R₁₁, SR₁₁, S(O)_(n)OR₁₁, or R₁₁S(O)_(n)R₁₁, whereinR₃, when substituted, has one or more substituents selected from F, Cl,Br, I, CN, NO₂, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₁-C₆ haloalkyl, C₂-C₆haloalkenyl, C₁-C₆ haloalkyloxy, C₂-C₆ haloalkenyloxy, C₃-C₁₀cycloalkyl, C₃-C₁₀ cycloalkenyl, C₃-C₁₀ halocycloalkyl, C₃-C₁₀halocycloalkenyl, OR₁₁, S(O)_(n)OR₁₁, C₆-C₂₀ aryl, or C₁-C₂₀heterocyclyl, wherein each of which may be unsubstituted or substitutedwith R₁₁;

R₅ is selected from hydrogen, F, Cl, Br, I, CN, NO₂, substituted orunsubstituted C₁-C₆ alkyl, substituted or unsubstituted C₂-C₆ alkenyl,substituted or unsubstituted C₁-C₆ alkoxy, C₃-C₁₀ cycloalkyl,substituted or unsubstituted C₆-C₂₀ aryl, substituted or unsubstitutedC₁-C₂₀ heterocyclyl, OR₁₁, C(═X₁)R₁₁, C(═X₁)OR₁₁, C(═X₁)N(R₁₁)₂,N(R₁₁)₂, N(R₁₁)C(═X₁)R₁₁, SR₁₁, S(O)_(n)OR₁₁, or R₁₁S(O)_(n)R₁₁, whereinR₅, when substituted, has one or more substituents selected from F, Cl,Br, I, CN, NO₂, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₁-C₆ haloalkyl, C₂-C₆haloalkenyl, C₁-C₆ haloalkyloxy, C₂-C₆ haloalkenyloxy, C₃-C₁₀cycloalkyl, C₃-C₁₀ cycloalkenyl, C₃-C₁₀ halocycloalkyl, C₃-C₁₀halocycloalkenyl, OR₁₁, S(O)_(n)OR₁₁, C₆-C₂₀ aryl, or C₁-C₂₀heterocyclyl, wherein each of which may be unsubstituted or substitutedwith R₁₁;

Z is Z₁, Z₂, Z₃, Z₄, Z₅, Z₆, Z₇ or Z₈;

R₆ is selected from hydrogen, F, Cl, Br, I, CN, NO₂, OR₁₁, substitutedor unsubstituted C₁-C₆ alkyl, substituted or unsubstituted C₂-C₆alkenyl, substituted or unsubstituted C₁-C₆ alkoxy, substituted orunsubstituted C₃-C₁₀ cycloalkyl, substituted or unsubstituted C₃-C₁₀halocycloalkyl substituted or unsubstituted C₃-C₁₀ cycloalkenyl,substituted or unsubstituted C₆-C₂₀ aryl, substituted or unsubstitutedC₁-C₂₀ heterocyclyl, C(═X₁)R₁₁, C(═X₁)OR₁₁, C(═X₁)N(R₁₁)₂, N(R₁₁)₂,N(R₁₁)C(═X₁)R₁₁, SR₁₁, S(O)_(n)OR₁₁, or R₁₁S(O)_(n)R₁₁, wherein R6, whensubstituted, has one or more substituents selected from F, Cl, Br, I,CN, NO₂, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl,C₁-C₆ haloalkyloxy, C₂-C₆ haloalkenyloxy, C₃-C₁₀ cycloalkyl, C₃-C₁₀cycloalkenyl, C₃-C₁₀ halocycloalkyl, C₃-C₁₀ halocycloalkenyl, oxo, OR₁₁,S(O)_(n)R₁₁, C₆-C₂₀ aryl, or C₁-C₂₀ heterocyclyl, wherein each of whichmay be unsubstituted or substituted with R₁₁;

R₇ is selected from hydrogen, F, Cl, Br, I, CN, NO₂, OR₁₁, substitutedor unsubstituted C₁-C₆ alkyl, substituted or unsubstituted C₂-C₆alkenyl, substituted or unsubstituted C₁-C₆ alkoxy, substituted orunsubstituted C₃-C₁₀ cycloalkyl, substituted or unsubstituted C₃-C₁₀halocycloalkyl substituted or unsubstituted C₃-C₁₀ cycloalkenyl,substituted or unsubstituted C₆-C₂₀ aryl, substituted or unsubstitutedC₁-C₂₀ heterocyclyl, C(═X₁)R₁₁, C(═X₁)OR₁₁, C(═X₁)N(R₁₁)₂, N(R₁₁)₂,N(R₁₁)C(═X₁)R₁₁, SR₁₁, S(O)_(n)OR₁₁, or R₁₁S(O)_(n)R₁₁, wherein R₇, whensubstituted, has one or more substituents selected from F, Cl, Br, I,CN, NO₂, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl,C₁-C₆ haloalkyloxy, C₂-C₆ haloalkenyloxy, C₃-C₁₀ cycloalkyl, C₃-C₁₀cycloalkenyl, C₃-C₁₀ halocycloalkyl, C₃-C₁₀ halocycloalkenyl, oxo, OR₁₁,S(O)_(n)R₁₁, C₆-C₂₀ aryl, or C₁-C₂₀ heterocyclyl, wherein each of whichmay be unsubstituted or substituted with R₁₁;

R₈ is selected from hydrogen, F, Cl, Br, I, CN, NO₂, OR₁₁, substitutedor unsubstituted C₁-C₆ alkyl, substituted or unsubstituted C₂-C₆alkenyl, substituted or unsubstituted C₁-C₆ alkoxy, substituted orunsubstituted C₃-C₁₀ cycloalkyl, substituted or unsubstituted C₃-C₁₀halocycloalkyl substituted or unsubstituted C₃-C₁₀ cycloalkenyl,substituted or unsubstituted C₆-C₂₀ aryl, substituted or unsubstitutedC₁-C₂₀ heterocyclyl, C(═X₁)R₁₁, C(═X₁)OR₁₁, C(═X₁)N(R₁₁)₂, N(R₁₁)₂,N(R₁₁)C(═X₁)R₁₁, SR₁₁, S(O)_(n)OR₁₁, or R₁₁S(O)_(n)R₁₁, wherein R₈, whensubstituted, has one or more substituents selected from F, Cl, Br, I,CN, NO₂, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl,C₁-C₆ haloalkyloxy, C₂-C₆ haloalkenyloxy, C₃-C₁₀ cycloalkyl, C₃-C₁₀cycloalkenyl, C₃-C₁₀ halocycloalkyl, C₃-C₁₀ halocycloalkenyl, oxo, OR₁₁,S(O)_(n)R₁₁, C₆-C₂₀ aryl, or C₁-C₂₀ heterocyclyl, wherein each of whichmay be unsubstituted or substituted with R₁₁;

R₉ is selected from hydrogen, F, Cl, Br, I, CN, NO₂, —OR₁₁, substitutedor unsubstituted C₁-C₆ alkyl, substituted or unsubstituted C₂-C₆alkenyl, substituted or unsubstituted C₁-C₆ alkoxy, substituted orunsubstituted C₃-C₁₀ cycloalkyl, substituted or unsubstituted C₃-C₁₀halocycloalkyl, substituted or unsubstituted C₃-C₁₀ cycloalkenyl,substituted or unsubstituted C₆-C₂₀ aryl, substituted or unsubstitutedC₁-C₂₀ heterocyclyl, C(═X₁)R₁₁, C(═X₁)OR₁₁, C(═X₁)N(R₁₁)₂, N(R₁₁)₂,N(R₁₁)C(═X₁)R₁₁, SR₁₁, S(O)_(n)OR₁₁, or R₁₁S(O)_(n)R₁₁, wherein R₉, whensubstituted, has one or more substituents selected from F, Cl, Br, I,CN, NO₂, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl,C₁-C₆ haloalkyloxy, C₂-C₆ haloalkenyloxy, C₃-C₁₀ cycloalkyl, C₃-C₁₀cycloalkenyl, C₃-C₁₀ halocycloalkyl, C₃-C₁₀ halocycloalkenyl, oxo, OR₁₁,S(O)_(n)R₁₁, C₆-C₂₀ aryl, or C₁-C₂₀ heterocyclyl, wherein each of whichmay be unsubstituted or substituted with R₁₁;

R₁₀ is selected from hydrogen, F, Cl, Br, I, CN, NO₂, OR₁₁, substitutedor unsubstituted C₁-C₆ alkyl, substituted or unsubstituted C₂-C₆alkenyl, substituted or unsubstituted C₁-C₆ alkoxy, substituted orunsubstituted C₃-C₁₀ cycloalkyl, substituted or unsubstituted C₃-C₁₀halocycloalkyl substituted or unsubstituted C₃-C₁₀ cycloalkenyl,substituted or unsubstituted C₆-C₂₀ aryl, substituted or unsubstitutedC₁-C₂₀ heterocyclyl, C(═X₁)R₁₁, C(═X₁)OR₁₁, C(═X₁)N(R₁₁)₂, N(R₁₁)₂,N(R₁₁)C(═X₁)R₁₁, SR₁₁, S(O)_(n)OR₁₁, or R₁₁S(O)_(n)R₁₁, wherein R₁₀,when substituted, has one or more substituents selected from F, Cl, Br,I, CN, NO₂, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₁-C₆ haloalkyl, C₂-C₆haloalkenyl, C₁-C₆ haloalkyloxy, C₂-C₆ haloalkenyloxy, C₃-C₁₀cycloalkyl, C₃-C₁₀ cycloalkenyl, C₃-C₁₀ halocycloalkyl, C₃-C₁₀halocycloalkenyl, oxo, OR₁₁, S(O)_(n)R₁₁, C₆-C₂₀ aryl, or C₁-C₂₀heterocyclyl, wherein each of which may be unsubstituted or substitutedwith R₁₁;

R₁₁ is selected from hydrogen, F, Cl, Br, I, CN, NO₂, substituted orunsubstituted C₁-C₆ alkyl, substituted or unsubstituted C₂-C₆ alkenyl,substituted or unsubstituted C₁-C₆ alkoxy, substituted or unsubstitutedC₂-C₆ alkenyloxy, substituted or unsubstituted C₃-C₁₀ cycloalkyl,substituted or unsubstituted C₃-C₁₀ cycloalkenyl, substituted orunsubstituted C₆-C₂₀ aryl, substituted or unsubstituted C₁-C₂₀heterocyclyl, substituted or unsubstituted S(O)_(n)C₁-C₆ alkyl, orsubstituted or unsubstituted N(C₁-C₆ alkyl)₂, wherein R₁₁, whensubstituted, has one or more substituents selected from F, Cl, Br, I,CN, NO₂, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl,C₁-C₆ haloalkyloxy, C₂-C₆ haloalkenyloxy, C₃-C₁₀ cycloalkyl, C₃-C₁₀cycloalkenyl, C₃-C₁₀ halocycloalkyl, C₃-C₁₀ halocycloalkenyl, OC₁-C₆alkyl, OC₁-C₆ haloalkyl, S(O)_(n)C₁-C₆alkyl, S(O)_(n)OC₁-C₆ alkyl,C₆-C₂₀ aryl, or C₁-C₂₀ heterocyclyl;

X₁=O or S;

n is 0, 1, or 2; and

x is 0 or 1.

In another embodiment, and in any combination with any of the previousor following embodiments, R₁, R₂, and R₄ are H.

In another embodiment, and in any combination with any of the previousor following embodiments, R₃ is selected from H, F, Cl, Br, or I,preferably, H or F.

In another embodiment, and in any combination with any of the previousor following embodiments, R₅ is hydrogen.

In another embodiment, and in any combination with any of the previousor following embodiments, Z is Z₅.

In another embodiment, and in any combination with any of the previousor following embodiments, R₆ and R₇ are independently selected fromhydrogen, substituted or unsubstituted C₁-C₆ haloalkyl and R₈ and R₉ arehydrogen.

While some embodiments have been described herein, other embodiments andcombinations of the described embodiments with other embodiments may bepossible.

In one embodiment, the pyridine triazole compounds of formula I may beprepared, as shown in Scheme 1, by reacting the triazole compound 1-1(prepared as described in Bioorganic & Medicinal Chemistry 2008, 16,9817) with an aryl/heterocyclic halide 1-2 in the presence of a catalystand a base in a polar aprotic solvent such as dioxane, at a temperatureof from about −78° C. to about 120° C. Non-limiting examples of thecatalysts may include bis-(triphenylphosphine) palladium (II) dichloride(Pd(PPh₃)₂Cl₂) and copper(I) iodide (CuI). Non-limiting examples of thebase may include a salt such as cesium fluoride (CsF).

In another embodiment, the pyridine triazole compounds of formula I maybe prepared, as shown in Scheme 2, by reacting 4-iodo-triazole compound2-1 (prepared as described in Bioorganic & Medicinal Chemistry 2008, 16,9817) with an aryl/heterocyclic boronic acid compound (2-2) in thepresence of a catalyst and a base in a suitable solvent system, such asa mixture of 1,4-dioxane and water, at a temperature of from about 25°C. to about 120° C. Non-limiting examples of the catalyst may includePd(PPh₃)₂Cl₂ and non-limiting examples of the base may include sodiumcarbonate (Na₂CO₃).

Pesticidally Acceptable Acid Addition Salts, Salt Derivatives, Solvates,Ester Derivatives, Polymorphs, Isotopes, Radionuclides and Stereoisomers

In some embodiments, the pyridine triazole compounds of formula I may beformulated into pesticidally acceptable acid addition salts. By way of anon-limiting example, an amine function can form salts withhydrochloric, hydrobromic, sulfuric, phosphoric, acetic, benzoic,citric, malonic, salicylic, malic, fumaric, oxalic, succinic, tartaric,lactic, gluconic, ascorbic, maleic, aspartic, benzenesulfonic,methanesulfonic, ethanesulfonic, hydroxymethanesulfonic,hydroxyethanesulfonic, and trifluoroacetic acids. Additionally, by wayof a non-limiting example, an acid function can form salts includingthose derived from alkali or alkaline earth metals and those derivedfrom ammonia and amines. Examples of preferred cations include sodium,potassium, and magnesium.

In some embodiments, the pyridine triazole compounds of formula I may beformulated into salt derivatives. By way of a non-limiting example, asalt derivative can be prepared by contacting a free base with asufficient amount of the desired acid to produce a salt. A free base maybe regenerated by treating the salt with a suitable dilute aqueous basesolution such as dilute aqueous sodium hydroxide (NaOH), potassiumcarbonate, ammonia, and sodium bicarbonate. As an example, in manycases, a pesticide, such as 2,4-D, is made more water-soluble byconverting it to its dimethylamine salt.

In further embodiments, the pyridine triazole compounds of formula I maybe formulated into stable complexes with a solvent, such that thecomplex remains intact after the non-complexed solvent is removed. Thesecomplexes are often referred to as “solvates.” However, it isparticularly desirable to form stable hydrates with water as thesolvent.

In some embodiments, the pyridine triazole compounds of formula I may bemade into ester derivatives. These ester derivatives can then be appliedin the same manner as the invention disclosed in this document isapplied.

In some embodiments, the pyridine triazole compounds of formula I may bemade as various crystal polymorphs. Polymorphism is important in thedevelopment of agrochemicals since different crystal polymorphs orstructures of the same molecule can have vastly different physicalproperties and biological performances.

In further embodiments, the pyridine triazole compounds of formula I maybe made with different isotopes. Of particular importance are moleculeshaving ²H (also known as deuterium) in place of ¹H.

In some embodiments, the pyridine triazole compounds of formula I may bemade with different radionuclides. Of particular importance aremolecules having ¹³C or ¹⁴C.

In some embodiments, the pyridine triazole compounds of formula I mayexist as one or more stereoisomers. Thus, certain molecules can beproduced as racemic mixtures. It will be appreciated by those skilled inthe art that one stereoisomer may be more active than the otherstereoisomers. Individual stereoisomers may be obtained by knownselective synthetic procedures, by conventional synthetic proceduresusing resolved starting materials, or by conventional resolutionprocedures. Certain molecules disclosed in this document can exist astwo or more isomers. The various isomers include geometric isomers,diastereomers, and enantiomers. Thus, the molecules disclosed in thisdocument include geometric isomers, racemic mixtures, individualstereoisomers, and optically active mixtures. It will be appreciated bythose skilled in the art that one isomer may be more active than theothers. The structures disclosed in the present disclosure are drawn inonly one geometric form for clarity, but are intended to represent allgeometric forms of the molecule.

Pesticidal Compositions

In one particular embodiment, a pesticidal composition comprises apyridine triazole compounds of formula I, or any agriculturallyacceptable salt thereof

In some embodiments, a pesticidal composition comprises a pyridinetriazole compounds of formula I or any agriculturally acceptable saltthereof, and a phytologically-acceptable inert carrier (e.g., solidcarrier, or liquid carrier).

In one embodiment, the pesticidal composition may further comprise atleast one additive selected from surfactant, a stabilizer, an emeticagent, a disintegrating agent, an antifoaming agent, a wetting agent, adispersing agent, a binding agent, dyes, or fillers.

In some embodiments, the pesticidal compositions may be in the form ofsolid. Non-limiting examples of the solid forms may include power, dustor granular formulations.

In other embodiments, the pesticidal compositions may be in the form ofliquid formulation. Examples of the liquid forms may include, but notlimited to, dispersion, suspension, emulsion or solution in appropriateliquid carrier.

In further embodiments, the pesticidal compositions may be in the formof liquid dispersion, wherein the pyridine triazole compounds of formulaI may be dispersed in water or other agriculturally suitable liquidcarrier.

In yet further embodiments, the pesticidal compositions may be in theform of solution in an appropriate organic solvent. In one embodiment,the spray oils, which are widely used in agricultural chemistry, may beused as an organic solvent for the pesticidal compositions.

The pesticidal composition may be used in conjunction (such as, in acompositional mixture, or a simultaneous or sequential application) withone or more compounds having acaricidal, algicidal, avicidal,bactericidal, fungicidal, herbicidal, insecticidal, molluscicidal,nematicidal, rodenticidal, and/or virucidal properties.

Furthermore, the pesticidal composition may be used in conjunction (suchas, in a compositional mixture, or a simultaneous or sequentialapplication) with one or more compounds that are antifeedants, birdrepellents, chemosterilants, herbicide safeners, insect attractants,insect repellents, mammal repellents, mating disrupters, plantactivators, plant growth regulators, and/or synergists.

Insecticides

Non-limiting examples of insecticides that may be used in combinationwith the pyridine triazole compounds of formula I may include1,2-dichloropropane, abamectin, acephate, acetamiprid, acethion,acetoprole, acrinathrin, acrylonitrile, alanycarb, aldicarb, aldoxycarb,aldrin, allethrin, allosamidin, allyxycarb, alpha-cypermethrin,alpha-ecdysone, α/p/ω-endosulfan, amidithion, aminocarb, amiton, amitonoxalate, amitraz, anabasine, athidathion, azadirachtin, azamethiphos,azinphos-ethyl, azinphos-methyl, azothoate, barium hexafluorosilicate,barthrin, bendiocarb, benfuracarb, bensultap, beta-cyfluthrin,beta-cypermethrin, bifenthrin, bioallethrin, bioethanomethrin,biopermethrin, bistrifluron, borax, boric acid, bromfenvinfos,bromocyclen, bromo-DDT, bromophos, bromophos-ethyl, bufencarb,buprofezin, butacarb, butathiofos, butocarboxim, butonate,butoxycarboxim, cadusafos, calcium arsenate, calcium polysulfide,camphechlor, carbanolate, carbaryl, carbofuran, carbon disulfide, carbontetrachloride, carbophenothion, carbosulfan, cartap, cartaphydrochloride, chlorantraniliprole, chlorbicyclen, chlordane,chlordecone, chlordimeform, chlordimeform hydrochloride, chlorethoxyfos,chlorfenapyr, chlorfenvinphos, chlorfluazuron, chlormephos, chloroform,chloropicrin, chlorphoxim, chlorprazophos, chlorpyrifos,chlorpyrifos-methyl, chlorthiophos, chromafenozide, cinerin I, cinerinII, cinerins, cismethrin, cloethocarb, closantel, clothianidin, copperacetoarsenite, copper arsenate, copper naphthenate, copper oleate,coumaphos, coumithoate, crotamiton, crotoxyphos, crufomate, cryolite,cyanofenphos, cyanophos, cyanthoate, cyantraniliprole, cyclethrin,cycloprothrin, cyfluthrin, cyhalothrin, cypermethrin, cyphenothrin,cyromazine, cythioate, DDT, decarbofuran, deltamethrin, demephion,demephion-O, demephion-S, demeton, demeton-methyl, demeton-O,demeton-O-methyl, demeton-S, demeton-S-methyl, demeton-S-methylsulphon,diafenthiuron, dialifos, diatomaceous earth, diazinon, dicapthon,dichlofenthion, dichlorvos, dicresyl, dicrotophos, dicyclanil, dieldrin,diflubenzuron, dilor, dimefluthrin, dimefox, dimetan, dimethoate,dimethrin, dimethylvinphos, dimetilan, dinex, dinex-diclexine, dinoprop,dinosam, dinotefuran, diofenolan, dioxabenzofos, dioxacarb, dioxathion,disulfoton, dithicrofos, d-limonene, DNOC, DNOC-ammonium,DNOC-potassium, DNOC-sodium, doramectin, ecdysterone, emamectin,emamectin benzoate, EMPC, empenthrin, endosulfan, endothion, endrin,EPN, epofenonane, eprinomectin, esdépalléthrine, esfenvalerate, etaphos,ethiofencarb, ethion, ethiprole, ethoate-methyl, ethoprophos, ethylformate, ethyl-DDD, ethylene dibromide, ethylene dichloride, ethyleneoxide, etofenprox, etrimfos, EXD, famphur, fenamiphos, fenazaflor,fenchlorphos, fenethacarb, fenfluthrin, fenitrothion, fenobucarb,fenoxacrim, fenoxycarb, fenpirithrin, fenpropathrin, fensulfothion,fenthion, fenthion-ethyl, fenvalerate, fipronil, flonicamid,flubendiamide (additionally resolved isomers thereof), flucofuron,flucycloxuron, flucythrinate, flufenerim, flufenoxuron, flufenprox,fluvalinate, fonofos, formetanate, formetanate hydrochloride,formothion, formparanate, formparanate hydrochloride, fosmethilan,fospirate, fosthietan, fufenozide, furathiocarb, furethrin,gamma-cyhalothrin, gamma-HCH, halfenprox, halofenozide, HCH, HEOD,heptachlor, heptenophos, heterophos, hexaflumuron, HHDN, hydramethylnon,hydrogen cyanide, hydroprene, hyquincarb, imidacloprid, imiprothrin,indoxacarb, iodomethane, IPSP, isazofos, isobenzan, isocarbophos,isodrin, isofenphos, isofenphos-methyl, isoprocarb, isoprothiolane,isothioate, isoxathion, ivermectin, jasmolin I, jasmolin II, jodfenphos,juvenile hormone I, juvenile hormone II, juvenile hormone III, kelevan,kinoprene, lambda-cyhalothrin, lead arsenate, lepimectin, leptophos,lindane, lirimfos, lufenuron, lythidathion, malathion, malonoben,mazidox, mecarbam, mecarphon, menazon, meperfluthrin, mephosfolan,mercurous chloride, mesulfenfos, metaflumizone, methacrifos,methamidophos, methidathion, methiocarb, methocrotophos, methomyl,methoprene, methothrin, methoxychlor, methoxyfenozide, methyl bromide,methyl isothiocyanate, methylchloroform, methylene chloride,metofluthrin, metolcarb, metoxadiazone, mevinphos, mexacarbate,milbemectin, milbemycin oxime, mipafox, mirex, molosultap,monocrotophos, monomehypo, monosultap, morphothion, moxidectin,naftalofos, naled, naphthalene, nicotine, nifluridide, nitenpyram,nithiazine, nitrilacarb, novaluron, noviflumuron, omethoate, oxamyl,oxydemeton-methyl, oxydeprofos, oxydisulfoton, para-dichlorobenzene,parathion, parathion-methyl, penfluron, pentachlorophenol, permethrin,phenkapton, phenothrin, phenthoate, phorate, phosalone, phosfolan,phosmet, phosnichlor, phosphamidon, phosphine, phoxim, phoxim-methyl,pirimetaphos, pirimicarb, pirimiphos-ethyl, pirimiphos-methyl, potassiumarsenite, potassium thiocyanate, pp′-DDT, prallethrin, precocene I,precocene II, precocene III, primidophos, profenofos, profluralin,profluthrin, promacyl, promecarb, propaphos, propetamphos, propoxur,prothidathion, prothiofos, prothoate, protrifenbute, pymetrozine,pyraclofos, pyrafluprole, pyrazophos, pyresmethrin, pyrethrin I,pyrethrin II, pyrethrins, pyridaben, pyridalyl, pyridaphenthion,pyrifluquinazon, pyrimidifen, pyrimitate, pyriprole, pyriproxyfen,quassia, quinalphos, quinalphos-methyl, quinothion, rafoxanide,resmethrin, rotenone, ryania, sabadilla, schradan, selamectin,silafluofen, silica gel, sodium arsenite, sodium fluoride, sodiumhexafluorosilicate, sodium thiocyanate, sophamide, spinetoram, spinosad,spiromesifen, spirotetramat, sulcofuron, sulcofuron-sodium, sulfluramid,sulfotep, sulfoxaflor, sulfuryl fluoride, sulprofos, tau-fluvalinate,tazimcarb, TDE, tebufenozide, tebufenpyrad, tebupirimfos, teflubenzuron,tefluthrin, temephos, TEPP, terallethrin, terbufos, tetrachloroethane,tetrachlorvinphos, tetramethrin, tetramethylfluthrin, Aeto-cypermethrin,thiacloprid, thiamethoxam, thicrofos, thiocarboxime, thiocyclam,thiocyclam oxalate, thiodicarb, thiofanox, thiometon, thiosultap,thiosultap-disodium, thiosultap-monosodium, thuringiensin, tolfenpyrad,tralomethrin, transfluthrin, transpermethrin, triarathene, triazamate,triazophos, trichlorfon, trichlormetaphos-3, trichloronat, trifenofos,triflumuron, trimethacarb, triprene, vamidothion, vaniliprole, XMC,xylylcarb, zeta-cypermethrin, or zolaprofos.

Acaricides

Non-limiting examples of acaricides that may be used in combination withthe pyridine triazole compounds of formula I may include acequinocyl,amidoflumet, arsenous oxide, azobenzene, azocyclotin, benomyl,benoxafos, benzoximate, benzyl benzoate, bifenazate, binapacryl,bromopropylate, chinomethionat, chlorbenside, chlorfenethol,chlorfenson, chlorfensulphide, chlorobenzilate, chloromebuform,chloromethiuron, chloropropylate, clofentezine, cyenopyrafen,cyflumetofen, cyhexatin, dichlofluanid, dicofol, dienochlor,diflovidazin, dinobuton, dinocap, dinocap-4, dinocap-6, dinocton,dinopenton, dinosulfon, dinoterbon, diphenyl sulfone, disulfiram,dofenapyn, etoxazole, fenazaquin, fenbutatin oxide, fenothiocarb,fenpyroximate, fenson, fentrifanil, fluacrypyrim, fluazuron,flubenzimine, fluenetil, flumethrin, fluorbenside, hexythiazox,mesulfen, MNAF, nikkomycins, proclonol, propargite, quintiofos,spirodiclofen, sulfiram, sulfur, tetradifon, tetranactin, tetrasul, orthioquinox.

Nematicides

Non-limiting examples of nematicides that may be used in combinationwith the pyridine triazole compounds of formula I may include1,3-dichloropropene, benclothiaz, dazomet, dazomet-sodium, DBCP, DCIP,diamidafos, fluensulfone, fosthiazate, furfural, imicyafos, isamidofos,isazofos, metam, metam-ammonium, metam-potassium, metam-sodium,phosphocarb, or thionazin.

Fungicides

Non-limiting examples of fungicides that may be used in combination withthe pyridine triazole compounds of formula I may include(3-ethoxypropyl)mercury bromide, 2-methoxyethylmercury chloride,2-phenylphenol, 8-hydroxyquinoline sulfate, 8-phenylmercurioxyquinoline,acibenzolar, acibenzolar-S-methyl, acypetacs, acypetacs-copper,acypetacs-zinc, aldimorph, allyl alcohol, ametoctradin, amisulbrom,ampropylfos, anilazine, aureofungin, azaconazole, azithiram,azoxystrobin, barium polysulfide, benalaxyl, benalaxyl-M, benodanil,benomyl, benquinox, bentaluron, benthiavalicarb,benthiavalicarb-isopropyl, benzalkonium chloride, benzamacril,benzamacril-isobutyl, benzamorf, benzohydroxamic acid, bethoxazin,binapacryl, biphenyl, bitertanol, bithionol, bixafen, blasticidin-S,Bordeaux mixture, boscalid, bromuconazole, bupirimate, Burgundy mixture,buthiobate, butylamine, calcium polysulfide, captafol, captan,carbamorph, carbendazim, carboxin, carpropamid, carvone, Cheshuntmixture, chinomethionat, chlobenthiazone, chloraniformethan, chloranil,chlorfenazole, chlorodinitronaphthalene, chloroneb, chloropicrin,chlorothalonil, chlorquinox, chlozolinate, climbazole, clotrimazole,copper acetate, copper carbonate, basic, copper hydroxide, coppernaphthenate, copper oleate, copper oxychloride, copper silicate, coppersulfate, copper zinc chromate, cresol, cufraneb, cuprobam, cuprousoxide, cyazofamid, cyclafuramid, cycloheximide, cyflufenamid, cymoxanil,cypendazole, cyproconazole, cyprodinil, dazomet, dazomet-sodium, DBCP,debacarb, decafentin, dehydroacetic acid, dichlofluanid, dichlone,dichlorophen, dichlozoline, diclobutrazol, diclocymet, diclomezine,diclomezine-sodium, dicloran, diethofencarb, diethyl pyrocarbonate,difenoconazole, diflumetorim, dimethirimol, dimethomorph, dimoxystrobin,diniconazole, diniconazole-M, dinobuton, dinocap, dinocap-4, dinocap-6,dinocton, dinopenton, dinosulfon, dinoterbon, diphenylamine,dipyrithione, disulfiram, ditalimfos, dithianon, DNOC, DNOC-ammonium,DNOC-potassium, DNOC-sodium, dodemorph, dodemorph acetate, dodemorphbenzoate, dodicin, dodicin-sodium, dodine, drazoxolon, edifenphos,epoxiconazole, etaconazole, etem, ethaboxam, ethirimol, ethoxyquin,ethylmercury 2,3-dihydroxypropyl mercaptide, ethylmercury acetate,ethylmercury bromide, ethylmercury chloride, ethylmercury phosphate,etridiazole, famoxadone, fenamidone, fenaminosulf, fenapanil, fenarimol,fenbuconazole, fenfuram, fenhexamid, fenitropan, fenoxanil, fenpiclonil,fenpropidin, fenpropimorph, fentin, fentin chloride, fentin hydroxide,ferbam, ferimzone, fluazinam, fludioxonil, flumetover, flumorph,fluopicolide, fluopyram, fluoroimide, fluotrimazole, fluoxastrobin,fluquinconazole, flusilazole, flusulfamide, flutianil, flutolanil,flutriafol, fluxapyroxad, folpet, formaldehyde, fosetyl,fosetyl-aluminium, fuberidazole, furalaxyl, furametpyr, furcarbanil,furconazole, furconazole-cis, furfural, furmecyclox, furophanate,glyodin, griseofulvin, guazatine, halacrinate, hexachlorobenzene,hexachlorobutadiene, hexaconazole, hexylthiofos, hydrargaphen,hymexazol, imazalil, imazalil nitrate, imazalil sulfate, imibenconazole,iminoctadine, iminoctadine triacetate, iminoctadine trialbesilate,iodomethane, ipconazole, iprobenfos, iprodione, iprovalicarb,isoprothiolane, isopyrazam, isotianil, isovaledione, kasugamycin,kresoxim-methyl, mancopper, mancozeb, mandipropamid, maneb, mebenil,mecarbinzid, mepanipyrim, mepronil, meptyldinocap, mercuric chloride,mercuric oxide, mercurous chloride, metalaxyl, metalaxyl-M, metam,metam-ammonium, metam-potassium, metam-sodium, metazoxolon, metconazole,methasulfocarb, methfuroxam, methyl bromide, methyl isothiocyanate,methylmercury benzoate, methylmercury dicyandiamide, methylmercurypentachlorophenoxide, metiram, metominostrobin, metrafenone,metsulfovax, milneb, myclobutanil, myclozolin,N-(ethylmercury)-p-toluenesulphonanilide, nabam, natamycin,nitrostyrene, nitrothal-isopropyl, nuarimol, OCH, octhilinone, ofurace,orysastrobin, oxadixyl, oxine-copper, oxpoconazole, oxpoconazolefumarate, oxycarboxin, pefurazoate, penconazole, pencycuron, penflufen,pentachlorophenol, penthiopyrad, phenylmercuriurea, phenylmercuryacetate, phenylmercury chloride, phenylmercury derivative ofpyrocatechol, phenylmercury nitrate, phenylmercury salicylate,phosdiphen, phthalide, picoxystrobin, piperalin, polycarbamate,polyoxins, polyoxorim, polyoxorim-zinc, potassium azide, potassiumpolysulfide, potassium thiocyanate, probenazole, prochloraz,procymidone, propamocarb, propamocarb hydrochloride, propiconazole,propineb, proquinazid, prothiocarb, prothiocarb hydrochloride,prothioconazole, pyracarbolid, pyraclostrobin, pyraclostrobin,pyrametostrobin, pyraoxystrobin, pyrazophos, pyribencarb, pyridinitril,pyrifenox, pyrimethanil, pyriofenone, pyroquilon, pyroxychlor,pyroxyfur, quinacetol, quinacetol sulfate, quinazamid, quinconazole,quinoxyfen, quintozene, rabenzazole, salicylanilide, sedaxane,silthiofam, simeconazole, sodium azide, sodium orthophenylphenoxide,sodium pentachlorophenoxide, sodium polysulfide, spiroxamine,streptomycin, sulfur, sultropen, TCMTB, tebuconazole, tebufloquin,tecloftalam, tecnazene, tecoram, tetraconazole, thiabendazole,thiadifluor, thicyofen, thifluzamide, thiochlorfenphim, thiomersal,thiophanate, thiophanate-methyl, thioquinox, thiram, tiadinil, tioxymid,tolclofos-methyl, tolylfluanid, tolylmercury acetate, triadimefon,triadimenol, triamiphos, triarimol, triazbutil, triazoxide, tributyltinoxide, trichlamide, tricyclazole, tridemorph, trifloxystrobin,triflumizole, triforine, triticonazole, uniconazole, uniconazole-P,validamycin, valifenalate, vinclozolin, zarilamid, zinc naphthenate,zineb, ziram, or zoxamide.

Herbicides

Non-limiting examples of herbicides that may be used in combination thepyridine triazole compounds of formula I may include 2,3,6-TBA,2,3,6-TBA-dimethylammonium, 2,3,6-TBA-sodium, 2,4,5-T,2,4,5-T-2-butoxypropyl, 2,4,5-T-2-ethylhexyl, 2,4,5-T-3-butoxypropyl,2,4,5-TB, 2,4,5-T-butometyl, 2,4,5-T-butotyl, 2,4,5-T-butyl,2,4,5-T-isobutyl, 2,4,5-T-isoctyl, 2,4,5-T-isopropyl, 2,4,5-T-methyl,2,4,5-T-pentyl, 2,4,5-T-sodium, 2,4,5-T-triethylammonium,2,4,5-T-trolamine, 2,4-D, 2,4-D-2-butoxypropyl, 2,4-D-2-ethylhexyl,2,4-D-3-butoxypropyl, 2,4-D-ammonium, 2,4-DB, 2,4-DB-butyl,2,4-DB-dimethylammonium, 2,4-DB-isoctyl, 2,4-DB-potassium,2,4-DB-sodium, 2,4-D-butotyl, 2,4-D-butyl, 2,4-D-diethylammonium,2,4-D-dimethylammonium, 2,4-D-diolamine, 2,4-D-dodecylammonium, 2,4-DEB,2,4-DEP, 2,4-D-ethyl, 2,4-D-heptylammonium, 2,4-D-isobutyl,2,4-D-isoctyl, 2,4-D-isopropyl, 2,4-D-isopropylammonium, 2,4-D-lithium,2,4-D-meptyl, 2,4-D-methyl, 2,4-D-octyl, 2,4-D-pentyl, 2,4-D-potassium,2,4-D-propyl, 2,4-D-sodium, 2,4-D-tefuryl, 2,4-D-tetradecylammonium,2,4-D-triethylammonium, 2,4-D-tris(2-hydroxypropyl)ammonium,2,4-D-trolamine, 3,4-DA, 3,4-DB, 3,4-DP, 4-CPA, 4-CPB, 4-CPP,acetochlor, acifluorfen, acifluorfen-methyl, acifluorfen-sodium,aclonifen, acrolein, alachlor, allidochlor, alloxydim, alloxydim-sodium,allyl alcohol, alorac, ametridione, ametryn, amibuzin, amicarbazone,amidosulfuron, amino cyclopyrachlor, amino cyclopyrachlor-methyl, aminocyclopyrachlor-potassium, aminopyralid, aminopyralid-potassium,aminopyralid-tris(2-hydroxypropyl)ammonium, amiprofos-methyl, amitrole,ammonium sulfamate, anilofos, anisuron, asulam, asulam-potassium,asulam-sodium, atraton, atrazine, azafenidin, azimsulfuron, aziprotryne,barban, BCPC, beflubutamid, benazolin, benazolin-dimethylammonium,benazolin-ethyl, benazolin-potassium, bencarbazone, benfluralin,benfuresate, bensulfuron, bensulfuron-methyl, bensulide, bentazone,bentazone-sodium, benzadox, benzadox-ammonium, benzfendizone, benzipram,benzobicyclon, benzofenap, benzofluor, benzoylprop, benzoylprop-ethyl,benzthiazuron, bicyclopyrone, bifenox, bilanafos, bilanafos-sodium,bispyribac, bispyribac-sodium, borax, bromacil, bromacil-lithium,bromacil-sodium, bromobonil, bromobutide, bromofenoxim, bromoxynil,bromoxynil butyrate, bromoxynil heptanoate, bromoxynil octanoate,bromoxynil-potassium, brompyrazon, butachlor, butafenacil, butamifos,butenachlor, buthidazole, buthiuron, butralin, butroxydim, buturon,butylate, cacodylic acid, cafenstrole, calcium chlorate, calciumcyanamide, cambendichlor, carbasulam, carbetamide, carboxazole,carfentrazone, carfentrazone-ethyl, CDEA, CEPC, chlomethoxyfen,chloramben, chloramben-ammonium, chloramben-diolamine,chloramben-methyl, chloramben-methylammonium, chloramben-sodium,chloranocryl, chlorazifop, chlorazifop-propargyl, chlorazine,chlorbromuron, chlorbufam, chloreturon, chlorfenac, chlorfenac-sodium,chlorfenprop, chlorfenprop-methyl, chlorflurazole, chlorflurenol,chlorflurenol-methyl, chloridazon, chlorimuron, chlorimuron-ethyl,chlornitrofen, chloropon, chlorotoluron, chloroxuron, chloroxynil,chlorprocarb, chlorpropham, chlorsulfuron, chlorthal,chlorthal-dimethyl, chlorthal-monomethyl, chlorthiamid, cinidon-ethyl,cinmethylin, cinosulfuron, cisanilide, clethodim, cliodinate,clodinafop, clodinafop-propargyl, clofop, clofop-isobutyl, clomazone,clomeprop, cloprop, cloproxydim, clopyralid, clopyralid-methyl,clopyralid-olamine, clopyralid-potassium,clopyralid-tris(2-hydroxypropyl)ammonium, cloransulam,cloransulam-methyl, CMA, copper sulfate, CPMF, CPPC, credazine, cresol,cumyluron, cyanamide, cyanatryn, cyanazine, cycloate, cyclosulfamuron,cycloxydim, cycluron, cyhalofop, cyhalofop-butyl, cyperquat, cyperquatchloride, cyprazine, cyprazole, cypromid, daimuron, dalapon,dalapon-calcium, dalapon-magnesium, dalapon-sodium, dazomet,dazomet-sodium, delachlor, desmedipham, desmetryn, di-allate, dicamba,dicamba-dimethylammonium, dicamba-diolamine, dicamba-isopropylammonium,dicamba-methyl, dicamba-olamine, dicamba-potassium, dicamba-sodium,dicamba-trolamine, dichlobenil, dichloralurea, dichlormate, dichlorprop,dichlorprop-2-ethylhexyl, dichlorprop-butotyl,dichlorprop-dimethylammonium, dichlorprop-ethylammonium,dichlorprop-isoctyl, dichlorprop-methyl, dichlorprop-P,dichlorprop-P-dimethylammonium, dichlorprop-potassium,dichlorprop-sodium, diclofop, diclofop-methyl, diclosulam, diethamquat,diethamquat dichloride, diethatyl, diethatyl-ethyl, difenopenten,difenopenten-ethyl, difenoxuron, difenzoquat, difenzoquat metilsulfate,diflufenican, diflufenzopyr, diflufenzopyr-sodium, dimefuron,dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimethenamid-P,dimexano, dimidazon, dinitramine, dinofenate, dinoprop, dinosam,dinoseb, dinoseb acetate, dinoseb-ammonium, dinoseb-diolamine,dinoseb-sodium, dinoseb-trolamine, dinoterb, dinoterb acetate,diphacinone-sodium, diphenamid, dipropetryn, diquat, diquat dibromide,disul, disul-sodium, dithiopyr, diuron, DMPA, DNOC, DNOC-ammonium,DNOC-potassium, DNOC-sodium, DSMA, EBEP, eglinazine, eglinazine-ethyl,endothal, endothal-diammonium, endothal-dipotassium, endothal-disodium,epronaz, EPTC, erbon, esprocarb, ethalfluralin, ethametsulfuron,ethametsulfuron-methyl, ethidimuron, ethiolate, ethofumesate, ethoxyfen,ethoxyfen-ethyl, ethoxysulfuron, etinofen, etnipromid, etobenzanid, EXD,fenasulam, fenoprop, fenoprop-3-butoxypropyl, fenoprop-butometyl,fenoprop-butotyl, fenoprop-butyl, fenoprop-isoctyl, fenoprop-methyl,fenoprop-potassium, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P,fenoxaprop-P-ethyl, fenoxasulfone, fenteracol, fenthiaprop,fenthiaprop-ethyl, fentrazamide, fenuron, fenuron TCA, ferrous sulfate,flamprop, flamprop-isopropyl, flamprop-M, flamprop-methyl,flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam,fluazifop, fluazifop-butyl, fluazifop-methyl, fluazifop-P,fluazifop-P-butyl, fluazolate, flucarbazone, flucarbazone-sodium,flucetosulfuron, fluchloralin, flufenacet, flufenican, flufenpyr,flufenpyr-ethyl, flumetsulam, flumezin, flumiclorac, flumiclorac-pentyl,flumioxazin, flumipropyn, fluometuron, fluorodifen, fluoroglycofen,fluoroglycofen-ethyl, fluoromidine, fluoronitrofen, fluothiuron,flupoxam, flupropacil, flupropanate, flupropanate-sodium,flupyrsulfuron, flupyrsulfuron-methyl-sodium, fluridone,flurochloridone, fluroxypyr, fluroxypyr-butometyl, fluroxypyr-meptyl,flurtamone, fluthiacet, fluthiacet-methyl, fomesafen, fomesafen-sodium,foramsulfuron, fosamine, fosamine-ammonium, furyloxyfen, glufosinate,glufosinate-ammonium, glufosinate-P, glufosinate-P-ammonium,glufosinate-P-sodium, glyphosate, glyphosate-diammonium,glyphosate-dimethylammonium, glyphosate-isopropylammonium,glyphosate-monoammonium, glyphosate-potassium, glyphosate-sesquisodium,glyphosate-trimesium, halosafen, halosulfuron, halosulfuron-methyl,haloxydine, haloxyfop, haloxyfop-etotyl, haloxyfop-methyl, haloxyfop-P,haloxyfop-P-etotyl, haloxyfop-P-methyl, haloxyfop-sodium,hexachloroacetone, hexaflurate, hexazinone, imazamethabenz,imazamethabenz-methyl, imazamox, imazamox-ammonium, imazapic,imazapic-ammonium, imazapyr, imazapyr-isopropylammonium, imazaquin,imazaquin-ammonium, imazaquin-methyl, imazaquin-sodium, imazethapyr,imazethapyr-ammonium, imazosulfuron, indanofan, indaziflam, iodobonil,iodomethane, iodosulfuron, iodosulfuron-methyl-sodium, ioxynil, ioxyniloctanoate, ioxynil-lithium, ioxynil-sodium, ipazine, ipfencarbazone,iprymidam, isocarbamid, isocil, isomethiozin, isonoruron, isopolinate,isopropalin, isoproturon, isouron, isoxaben, isoxachlortole,isoxaflutole, isoxapyrifop, karbutilate, ketospiradox, lactofen,lenacil, linuron, MAA, MAMA, MCPA, MCPA-2-ethylhexyl, MCPA-butotyl,MCPA-butyl, MCPA-dimethylammonium, MCPA-diolamine, MCPA-ethyl,MCPA-isobutyl, MCPA-isoctyl, MCPA-isopropyl, MCPA-methyl, MCPA-olamine,MCPA-potassium, MCPA-sodium, MCPA-thioethyl, MCPA-trolamine, MCPB,MCPB-ethyl, MCPB-methyl, MCPB-sodium, mecoprop, mecoprop-2-ethylhexyl,mecoprop-dimethylammonium, mecoprop-diolamine, mecoprop-ethadyl,mecoprop-isoctyl, mecoprop-methyl, mecoprop-P,mecoprop-P-dimethylammonium, mecoprop-P-isobutyl, mecoprop-potassium,mecoprop-P-potassium, mecoprop-sodium, mecoprop-trolamine, medinoterb,medinoterb acetate, mefenacet, mefluidide, mefluidide-diolamine,mefluidide-potassium, mesoprazine, mesosulfuron, mesosulfuron-methyl,mesotrione, metam, metam-ammonium, metamifop, metamitron,metam-potassium, metam-sodium, metazachlor, metazosulfuron, metflurazon,methabenzthiazuron, methalpropalin, methazole, methiobencarb,methiozolin, methiuron, methometon, methoprotryne, methyl bromide,methyl isothiocyanate, methyldymron, metobenzuron, metolachlor,metosulam, metoxuron, metribuzin, metsulfuron, metsulfuron-methyl,molinate, monalide, monisouron, monochloroacetic acid, monolinuron,monuron, monuron TCA, morfamquat, morfamquat dichloride, MSMA,naproanilide, napropamide, naptalam, naptalam-sodium, neburon,nicosulfuron, nipyraclofen, nitralin, nitrofen, nitrofluorfen,norflurazon, noruron, OCH, orbencarb, ortho-dichlorobenzene,orthosulfamuron, oryzalin, oxadiargyl, oxadiazon, oxapyrazon,oxapyrazon-dimolamine, oxapyrazon-sodium, oxasulfuron, oxaziclomefone,oxyfluorfen, parafluron, paraquat, paraquat dichloride, paraquatdimetilsulfate, pebulate, pelargonic acid, pendimethalin, penoxsulam,pentachlorophenol, pentanochlor, pentoxazone, perfluidone, pethoxamid,phenisopham, phenmedipham, phenmedipham-ethyl, phenobenzuron,phenylmercury acetate, picloram, picloram-2-ethylhexyl,picloram-isoctyl, picloram-methyl, picloram-olamine, picloram-potassium,picloram-triethylammonium, picloram-tris(2-hydroxypropyl)ammonium,picolinafen, pinoxaden, piperophos, potassium arsenite, potassium azide,potassium cyanate, pretilachlor, primisulfuron, primisulfuron-methyl,procyazine, prodiamine, profluazol, profluralin, profoxydim,proglinazine, proglinazine-ethyl, prometon, prometryn, propachlor,propanil, propaquizafop, propazine, propham, propisochlor,propoxycarbazone, propoxycarbazone-sodium, propyrisulfuron, propyzamide,prosulfalin, prosulfocarb, prosulfuron, proxan, proxan-sodium,prynachlor, pydanon, pyraclonil, pyraflufen, pyraflufen-ethyl,pyrasulfotole, pyrazolynate, pyrazosulfuron, pyrazosulfuron-ethyl,pyrazoxyfen, pyribenzoxim, pyributicarb, pyriclor, pyridafol, pyridate,pyriftalid, pyriminobac, pyriminobac-methyl, pyrimisulfan, pyrithiobac,pyrithiobac-sodium, pyroxasulfone, pyroxsulam, quinclorac, quinmerac,quinoclamine, quinonamid, quizalofop, quizalofop-ethyl, quizalofop-P,quizalofop-P-ethyl, quizalofop-P-tefuryl, rhodethanil, rimsulfuron,saflufenacil, sebuthylazine, secbumeton, sethoxydim, siduron, simazine,simeton, simetryn, SMA, S-metolachlor, sodium arsenite, sodium azide,sodium chlorate, sulcotrione, sulfallate, sulfentrazone, sulfometuron,sulfometuron-methyl, sulfosulfuron, sulfuric acid, sulglycapin, swep,TCA, TCA-ammonium, TCA-calcium, TCA-ethadyl, TCA-magnesium, TCA-sodium,tebutam, tebuthiuron, tefuryltrione, tembotrione, tepraloxydim,terbacil, terbucarb, terbuchlor, terbumeton, terbuthylazine, terbutryn,tetrafluron, thenylchlor, thiazafluron, thiazopyr, thidiazimin,thidiazuron, thiencarbazone, thiencarbazone-methyl, thifensulfuron,thifensulfuron-methyl, thiobencarb, tiocarbazil, tioclorim, topramezone,tralkoxydim, tri-allate, triasulfuron, triaziflam, tribenuron,tribenuron-methyl, tricamba, triclopyr, triclopyr-butotyl,triclopyr-ethyl, triclopyr-triethylammonium, tridiphane, trietazine,trifloxysulfuron, trifloxysulfuron-sodium, trifluralin, triflusulfuron,triflusulfuron-methyl, trifop, trifop-methyl, trifopsime,trihydroxytriazine, trimeturon, tripropindan, tritac, tritosulfuron,vernolate, or xylachlor.

Biopesticides

The pyridine triazole compounds of formula I may also be used incombination (such as in a compositional mixture, or a simultaneous orsequential application) with one or more biopesticides. The term“biopesticide” is used for microbial biological pest control agents thatare applied in a similar manner to chemical pesticides. Commonly theseare bacterial, but there are also examples of fungal control agents,including Trichoderma spp. and Ampelomyces quisqualis (a control agentfor grape powdery mildew). Bacillus subtilis are used to control plantpathogens. Weeds and rodents have also been controlled with microbialagents. One well-known insecticide example is Bacillus thuringiensis, abacterial disease of Lepidoptera, Coleoptera, and Diptera. Because ithas little effect on other organisms, it is considered moreenvironmentally friendly than synthetic pesticides. Biologicalinsecticides include products based on:

-   -   1. entomopathogenic fungi (e.g. Metarhizium anisopliae);    -   2. entomopathogenic nematodes (e.g. Steinernema feltiae); and    -   3. entomopathogenic viruses (e.g. Cydia pomonella granulovirus).

Other examples of entomopathogenic organisms include, but are notlimited to, baculoviruses, bacteria and other prokaryotic organisms,fungi, protozoa and Microsproridia. Biologically derived insecticidesinclude, but not limited to, rotenone, veratridine, as well as microbialtoxins; insect tolerant or resistant plant varieties; and organismsmodified by recombinant DNA technology to either produce insecticides orto convey an insect resistant property to the genetically modifiedorganism. In one embodiment, the molecules of Formula One may be usedwith one or more biopesticides in the area of seed treatments and soilamendments. The Manual of Biocontrol Agents gives a review of theavailable biological insecticide (and other biology-based control)products. Copping L. G. (ed.) (2004). The Manual of Biocontrol Agents(formerly the Biopesticide Manual) 3rd Edition. British Crop ProductionCouncil (BCPC), Farnham, Surrey UK.

Other Active Compounds

The pyridine triazole compounds of formula I may also be used incombination (such as in a compositional mixture, or a simultaneous orsequential application) with one or more of the following:

-   -   1.        3-(4-chloro-2,6-dimethylphenyl)-4-hydroxy-8-oxa-1-azaspiro[4,5]dec-3-en-2-one;    -   2.        3-(4′-chloro-2,4-dimethyl[1,1′-biphenyl]-3-yl)-4-hydroxy-8-oxa-1-azaspiro[4,5]dec-3-en-2-one;    -   3. 4-[[(6-chloro-3-pyridinyl)methyl]methylamino]-2(5H)-furanone;    -   4.        4-[[(6-chloro-3-pyridinyl)methyl]cyclopropylamino]-2(5H)-furanone;    -   5.        3-chloro-N2-[(1S)-1-methyl-2-(methylsulfonyl)ethyl]-N1-[2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]-1,2-benzenedicarboxamide;    -   6. 2-cyano-N-ethyl-4-fluoro-3-methoxy-benenesulfonamide;    -   7. 2-cyano-N-ethyl-3-methoxy-benzenesulfonamide;    -   8.        2-cyano-3-difluoromethoxy-N-ethyl-4-fluoro-benzenesulfonamide;    -   9. 2-cyano-3-fluoromethoxy-N-ethyl-benzenesulfonamide;    -   10. 2-cyano-6-fluoro-3-methoxy-N,N-dimethyl-benzenesulfonamide;    -   11.        2-cyano-N-ethyl-6-fluoro-3-methoxy-N-methyl-benzenesulfonamide;    -   12. 2-cyano-3-difluoromethoxy-N,N-dimethylbenzenesulfon-amide;    -   13.        3-(difluoromethyl)-N-[2-(3,3-dimethylbutyl)phenyl]-1-methyl-1H-pyrazole-4-carboxamide;    -   14.        N-ethyl-2,2-dimethylpropionamide-2-(2,6-dichloro-α,α,α-trifluoro-p-tolyl)        hydrazone;    -   15.        N-ethyl-2,2-dichloro-1-methylcyclopropane-carboxamide-2-(2,6-dichloro-α,α,α-trifluoro-p-tolyl)        hydrazone nicotine;    -   16.        O-{(E−)-[2-(4-chloro-phenyl)-2-cyano-1-(2-trifluoromethylphenyl)-vinyl]}S-methyl        thiocarbonate;    -   17.        (E)-N1-[(2-chloro-1,3-thiazol-5-ylmethyl)]-N2-cyano-N1-methylacetamidine;    -   18.        1-(6-chloropyridin-3-ylmethyl)-7-methyl-8-nitro-1,2,3,5,6,7-hexahydro-imidazo[1,2-a]pyridin-5-ol;    -   19. 4-[4-chlorophenyl-(2-butylidine-hydrazono)methyl)]phenyl        mesylate; and    -   20.        N-ethyl-2,2-dichloro-1-methylcyclopropanecarboxamide-2-(2,6-dichloro-α,α,α-trifluoro-p-tolyl)hydrazone.

The pyridine triazole compounds of formula I may also be used incombination (such as in a compositional mixture, or a simultaneous orsequential application) with one or more compounds in the followinggroups: algicides, antifeedants, avicides, bactericides, birdrepellents, chemosterilants, herbicide safeners, insect attractants,insect repellents, mammal repellents, mating disrupters, molluscicides,plant activators, plant growth regulators, rodenticides, or virucides.

Synergistic Mixtures and Synergists

The pyridine triazole compounds of formula I may be used in combinationwith at least one other insecticides to form a synergistic mixture wherethe mode of action of such compounds compared to the mode of action ofthe pyridine triazole compounds of formula I are the same, similar, ordifferent. Examples of modes of action may include, but are not limitedto: acetylcholinesterase inhibitor; sodium channel modulator; chitinbiosynthesis inhibitor; GABA-gated chloride channel antagonist; GABA andglutamate-gated chloride channel agonist; acetylcholine receptoragonist; MET I inhibitor; Mg-stimulated ATPase inhibitor; nicotinicacetylcholine receptor; Midgut membrane disrupter; oxidativephosphorylation disrupter, or ryanodine receptor (RyRs).

Additionally, the pyridine triazole compounds of formula I may be usedin combination with at least one of fungicides, acaricides, herbicidesor nematicides to form a synergistic mixture.

Furthermore, the pyridine triazole compounds of formula I may be used incombination with other active compounds, such as the compounds under theheading “OTHER ACTIVE COMPOUNDS,” algicides, avicides, bactericides,molluscicides, rodenticides, virucides, herbicide safeners, adjuvants,and/or surfactants to form a synergistic mixture. Moreover, thefollowing compounds are known as synergists and may be used incombination with the pyridine triazole compounds of formula I: piperonylbutoxide, piprotal, propyl isome, sesamex, sesamolin, sulfoxide, andtribufos.

Formulations

A pesticide is rarely suitable for application in its pure form. It isusually necessary to add other substances so that the pesticide can beused at the required concentration and in an appropriate form,permitting ease of application, handling, transportation, storage, andmaximum pesticide activity. Thus, pesticides are formulated into, forexample, baits, concentrated emulsions, dusts, emulsifiableconcentrates, fumigants, gels, granules, microencapsulations, seedtreatments, suspension concentrates, suspoemulsions, tablets, watersoluble liquids, water dispersible granules or dry flowables, wettablepowders, and ultra low volume solutions. For further information onformulation types see “Catalogue of Pesticide Formulation Types andInternational Coding System” Technical Monograph n°2, 5th Edition byCropLife International (2002).

Pesticides are applied most often as aqueous suspensions or emulsionsprepared from concentrated formulations of such pesticides. Suchwater-soluble, water-suspendable, or emulsifiable formulations areeither solids, usually known as wettable powders, or water dispersiblegranules, or liquids usually known as emulsifiable concentrates, oraqueous suspensions. Wettable powders, which may be compacted to formwater dispersible granules, comprise an intimate mixture of thepesticide, a carrier, and surfactants. The concentration of thepesticide is usually from about 10% to about 90% by weight. The carrieris usually selected from among the attapulgite clays, themontmorillonite clays, the diatomaceous earths, or the purifiedsilicates. Effective surfactants, comprising from about 0.5% to about10% of the wettable powder, are found among sulfonated lignins,condensed naphthalenesulfonates, naphthalenesulfonates,alkylbenzenesulfonates, alkyl sulfates, and non-ionic surfactants suchas ethylene oxide adducts of alkyl phenols.

Emulsifiable concentrates of pesticides comprise a convenientconcentration of a pesticide, such as from about 50 to about 500 gramsper liter of liquid dissolved in a carrier that is either a watermiscible solvent or a mixture of water-immiscible organic solvent andemulsifiers. Useful organic solvents include aromatics, especiallyxylenes and petroleum fractions, especially the high-boilingnaphthalenic and olefinic portions of petroleum such as heavy aromaticnaphtha. Other organic solvents may also be used, such as the terpenicsolvents including rosin derivatives, aliphatic ketones such ascyclohexanone, and complex alcohols such as 2-ethoxyethanol. Suitableemulsifiers for emulsifiable concentrates are selected from conventionalanionic and non-ionic surfactants.

Aqueous suspensions comprise suspensions of water-insoluble pesticidesdispersed in an aqueous carrier at a concentration in the range fromabout 5% to about 50% by weight. Suspensions are prepared by finelygrinding the pesticide and vigorously mixing it into a carrier comprisedof water and surfactants. Ingredients, such as inorganic salts andsynthetic or natural gums may also be added, to increase the density andviscosity of the aqueous carrier. It is often most effective to grindand mix the pesticide at the same time by preparing the aqueous mixtureand homogenizing it in an implement such as a sand mill, ball mill, orpiston-type homogenizer.

Pesticides may also be applied as granular compositions that areparticularly useful for applications to the soil. Granular compositionsusually contain from about 0.5% to about 10% by weight of the pesticide,dispersed in a carrier that comprises clay or a similar substance. Suchcompositions are usually prepared by dissolving the pesticide in asuitable solvent and applying it to a granular carrier which has beenpre-formed to the appropriate particle size, in the range of from about0.5 to about 3 mm. Such compositions may also be formulated by making adough or paste of the carrier and compound and crushing and drying toobtain the desired granular particle size.

Dusts containing a pesticide are prepared by intimately mixing thepesticide in powdered form with a suitable dusty agricultural carrier,such as kaolin clay, ground volcanic rock, and the like. Dusts cansuitably contain from about 1% to about 10% of the pesticide. They canbe applied as a seed dressing or as a foliage application with a dustblower machine.

It is equally practical to apply a pesticide in the form of a solutionin an appropriate organic solvent, usually petroleum oil, such as thespray oils, which are widely used in agricultural chemistry.

Pesticides can also be applied in the form of an aerosol composition. Insuch compositions the pesticide is dissolved or dispersed in a carrier,which is a pressure-generating propellant mixture. The aerosolcomposition is packaged in a container from which the mixture isdispensed through an atomizing valve.

Pesticide baits are formed when the pesticide is mixed with food or anattractant or both. When the pests eat the bait they also consume thepesticide. Baits may take the form of granules, gels, flowable powders,liquids, or solids. They can be used in pest harborages.

Fumigants are pesticides that have a relatively high vapor pressure andhence can exist as a gas in sufficient concentrations to kill pests insoil or enclosed spaces. The toxicity of the fumigant is proportional toits concentration and the exposure time. They are characterized by agood capacity for diffusion and act by penetrating the pest'srespiratory system or being absorbed through the pest's cuticle.Fumigants are applied to control stored product pests under gas proofsheets, in gas sealed rooms or buildings or in special chambers.

Pesticides can be microencapsulated by suspending the pesticideparticles or droplets in plastic polymers of various types. By alteringthe chemistry of the polymer or by changing factors in the processing,microcapsules can be formed of various sizes, solubility, wallthicknesses, and degrees of penetrability. These factors govern thespeed with which the active ingredient within is released, which inturn, affects the residual performance, speed of action, and odor of theproduct.

Oil solution concentrates are made by dissolving pesticide in a solventthat will hold the pesticide in solution. Oil solutions of a pesticideusually provide faster knockdown and kill of pests than otherformulations due to the solvents themselves having pesticidal action andthe dissolution of the waxy covering of the integument increasing thespeed of uptake of the pesticide. Other advantages of oil solutionsinclude better storage stability, better penetration of crevices, andbetter adhesion to greasy surfaces.

Another embodiment is an oil-in-water emulsion, wherein the emulsioncomprises oily globules which are each provided with a lamellar liquidcrystal coating and are dispersed in an aqueous phase, wherein each oilyglobule comprises at least one compound which is agriculturally active,and is individually coated with a monolamellar or oligolamellar layercomprising: (1) at least one non-ionic lipophilic surface-active agent,(2) at least one non-ionic hydrophilic surface-active agent and (3) atleast one ionic surface-active agent, wherein the globules having a meanparticle diameter of less than 800 nanometers. Further information onthe embodiment is disclosed in U.S. patent publication 20070027034published Feb. 1, 2007, having patent application Ser. No. 11/495,228.For ease of use, this embodiment will be referred to as “OIWE.”

For further information consult “Insect Pest Management” 2nd Edition byD. Dent, copyright CAB International (2000). Additionally, for moredetailed information consult “Handbook of Pest Control—The Behavior,Life History, and Control of Household Pests” by Arnold Mallis, 9thEdition, copyright 2004 by GIE Media Inc.

Other Formulation Components

Generally, when the pyridine triazole compounds of formula I or anyagriculturally acceptable salt thereof, are used in a formulation, suchformulation can also contain other components. These components include,but are not limited to, (this is a non-exhaustive and non-mutuallyexclusive list) wetters, spreaders, stickers, penetrants, buffers,sequestering agents, drift reduction agents, compatibility agents,anti-foam agents, cleaning agents, and emulsifiers. A few components aredescribed forthwith.

A wetting agent is a substance that when added to a liquid increases thespreading or penetration power of the liquid by reducing the interfacialtension between the liquid and the surface on which it is spreading.Wetting agents are used for two main functions in agrochemicalformulations: during processing and manufacture to increase the rate ofwetting of powders in water to make concentrates for soluble liquids orsuspension concentrates; and during mixing of a product with water in aspray tank to reduce the wetting time of wettable powders and to improvethe penetration of water into water-dispersible granules. Examples ofwetting agents used in wettable powder, suspension concentrate, andwater-dispersible granule formulations are: sodium lauryl sulfate;sodium dioctyl sulfosuccinate; alkyl phenol ethoxylates; and aliphaticalcohol ethoxylates.

A dispersing agent is a substance which adsorbs onto the surface ofparticles and helps to preserve the state of dispersion of the particlesand prevents them from reaggregating. Dispersing agents are added toagrochemical formulations to facilitate dispersion and suspension duringmanufacture, and to ensure the particles redisperse into water in aspray tank. They are widely used in wettable powders, suspensionconcentrates and water-dispersible granules. Surfactants that are usedas dispersing agents have the ability to adsorb strongly onto a particlesurface and provide a charged or steric barrier to reaggregation ofparticles. The most commonly used surfactants are anionic, non-ionic, ormixtures of the two types. For wettable powder formulations, the mostcommon dispersing agents are sodium lignosulfonates. For suspensionconcentrates, very good adsorption and stabilization are obtained usingpolyelectrolytes, such as sodium naphthalene sulfonate formaldehydecondensates. Tristyrylphenol ethoxylate phosphate esters are also used.Non-ionics such as alkylarylethylene oxide condensates and EO-PO blockcopolymers are sometimes combined with anionics as dispersing agents forsuspension concentrates. In recent years, new types of very highmolecular weight polymeric surfactants have been developed as dispersingagents. These have very long hydrophobic “backbones” and a large numberof ethylene oxide chains forming the “teeth” of a “comb” surfactant.These high molecular weight polymers can give very good long-termstability to suspension concentrates because the hydrophobic backboneshave many anchoring points onto the particle surfaces. Examples ofdispersing agents used in agrochemical formulations are: sodiumlignosulfonates; sodium naphthalene sulfonate formaldehyde condensates;tristyrylphenol ethoxylate phosphate esters; aliphatic alcoholethoxylates; alkyl ethoxylates; EO-PO block copolymers; and graftcopolymers.

An emulsifying agent is a substance which stabilizes a suspension ofdroplets of one liquid phase in another liquid phase. Without theemulsifying agent the two liquids would separate into two immiscibleliquid phases. The most commonly used emulsifier blends containalkylphenol or aliphatic alcohol with twelve or more ethylene oxideunits and the oil-soluble calcium salt of dodecylbenzenesulfonic acid. Arange of hydrophile-lipophile balance (“HLB”) values from 8 to 18 willnormally provide good stable emulsions. Emulsion stability can sometimesbe improved by the addition of a small amount of an EO-PO blockcopolymer surfactant.

A solubilizing agent is a surfactant which will form micelles in waterat concentrations above the critical micelle concentration. The micellesare then able to dissolve or solubilize water-insoluble materials insidethe hydrophobic part of the micelle. The types of surfactants usuallyused for solubilization are non-ionics, sorbitan monooleates, sorbitanmonooleate ethoxylates, and methyl oleate esters.

Surfactants are sometimes used, either alone or with other additivessuch as mineral or vegetable oils as adjuvants to spray-tank mixes toimprove the biological performance of the pesticide on the target. Thetypes of surfactants used for bioenhancement depend generally on thenature and mode of action of the pesticide. However, they are oftennon-ionics such as: alkyl ethoxylates; linear aliphatic alcoholethoxylates; aliphatic amine ethoxylates.

A carrier or diluent in an agricultural formulation is a material addedto the pesticide to give a product of the required strength. Carriersare usually materials with high absorptive capacities, while diluentsare usually materials with low absorptive capacities. Carriers anddiluents are used in the formulation of dusts, wettable powders,granules and water-dispersible granules.

Organic solvents are used mainly in the formulation of emulsifiableconcentrates, oil-in-water emulsions, suspoemulsions, and ultra lowvolume formulations, and to a lesser extent, granular formulations.Sometimes mixtures of solvents are used. The first main groups ofsolvents are aliphatic paraffinic oils such as kerosene or refinedparaffins. The second main group (and the most common) comprises thearomatic solvents such as xylene and higher molecular weight fractionsof C9 and C10 aromatic solvents. Chlorinated hydrocarbons are useful ascosolvents to prevent crystallization of pesticides when the formulationis emulsified into water. Alcohols are sometimes used as cosolvents toincrease solvent power. Other solvents may include vegetable oils, seedoils, and esters of vegetable and seed oils.

Thickeners or gelling agents are used mainly in the formulation ofsuspension concentrates, emulsions and suspoemulsions to modify therheology or flow properties of the liquid and to prevent separation andsettling of the dispersed particles or droplets. Thickening, gelling,and anti-settling agents generally fall into two categories, namelywater-insoluble particulates and water-soluble polymers. It is possibleto produce suspension concentrate formulations using clays and silicas.Examples of these types of materials, include, but are not limited to,montmorillonite, bentonite, magnesium aluminum silicate, andattapulgite. Water-soluble polysaccharides have been used asthickening-gelling agents for many years. The types of polysaccharidesmost commonly used are natural extracts of seeds and seaweeds or aresynthetic derivatives of cellulose. Examples of these types of materialsinclude, but are not limited to, guar gum; locust bean gum; carrageenam;alginates; methyl cellulose; sodium carboxymethyl cellulose (SCMC);hydroxyethyl cellulose (HEC). Other types of anti-settling agents arebased on modified starches, polyacrylates, polyvinyl alcohol andpolyethylene oxide. Another good anti-settling agent is xanthan gum.

Microorganisms can cause spoilage of formulated products. Thereforepreservation agents are used to eliminate or reduce their effect.Examples of such agents include, but are not limited to: propionic acidand its sodium salt; sorbic acid and its sodium or potassium salts;benzoic acid and its sodium salt; p-hydroxybenzoic acid sodium salt;methyl p-hydroxybenzoate; and 1,2-benzisothiazolin-3-one (BIT).

The presence of surfactants often causes water-based formulations tofoam during mixing operations in production and in application through aspray tank. In order to reduce the tendency to foam, anti-foam agentsare often added either during the production stage or before fillinginto bottles. Generally, there are two types of anti-foam agents, namelysilicones and non-silicones. Silicones are usually aqueous emulsions ofdimethyl polysiloxane, while the non-silicone anti-foam agents arewater-insoluble oils, such as octanol and nonanol, or silica. In bothcases, the function of the anti-foam agent is to displace the surfactantfrom the air-water interface.

“Green” agents (e.g., adjuvants, surfactants, solvents) can reduce theoverall environmental footprint of crop protection formulations. Greenagents are biodegradable and generally derived from natural and/orsustainable sources, e.g. plant and animal sources. Specific examplesare: vegetable oils, seed oils, and esters thereof, also alkoxylatedalkyl polyglucosides.

For further information, see “Chemistry and Technology of AgrochemicalFormulations” edited by D. A. Knowles, copyright 1998 by Kluwer AcademicPublishers. Also see “Insecticides in Agriculture andEnvironment—Retrospects and Prospects” by A. S. Perry, I. Yamamoto, I.Ishaaya, and R. Perry, copyright 1998 by Springer-Verlag.

Pesticidal Activities

The disclosed pesticidal compositions may be used, for example, asnematicides, acaricides, pesticides, insecticides, miticides, and/ormolluscicides.

In one particular embodiment, a method of controlling pests comprisesapplying a pesticidal composition comprising a pyridine triazolecompounds of formula I or any agriculturally acceptable salt thereofnear a population of pests.

The pyridine triazole compounds of formula I are generally used inamounts from about 0.01 grams per hectare to about 5000 grams perhectare to provide control. Amounts from about 0.1 grams per hectare toabout 500 grams per hectare are generally preferred, and amounts fromabout 1 gram per hectare to about 50 grams per hectare are generallymore preferred.

The area to which a pyridine triazole compounds of formula I is appliedcan be any area inhabited (or maybe inhabited, or traversed by) a pest,for example: where crops, trees, fruits, cereals, fodder species, vines,turf and ornamental plants, are growing; where domesticated animals areresiding; the interior or exterior surfaces of buildings (such as placeswhere grains are stored), the materials of construction used in building(such as impregnated wood), and the soil around buildings. Particularcrop areas to use a molecule of Formula One include areas where apples,corn, sunflowers, cotton, soybeans, canola, wheat, rice, sorghum,barley, oats, potatoes, oranges, alfalfa, lettuce, strawberries,tomatoes, peppers, crucifers, pears, tobacco, almonds, sugar beets,beans and other valuable crops are growing or the seeds thereof aregoing to be planted. It is also advantageous to use ammonium sulfatewith a 3-(thiazol-2-yl)pyridine 1-oxide compound when growing variousplants.

Controlling pests generally means that pest populations, pest activity,or both, are reduced in an area. This can come about when: pestpopulations are repulsed from an area; when pests are incapacitated inor around an area; or pests are exterminated, in whole, or in part, inor around an area. Of course, a combination of these results can occur.Generally, pest populations, activity, or both are desirably reducedmore than fifty percent, preferably more than 90 percent. Generally, thearea is not in or on a human; consequently, the locus is generally anon-human area.

The pyridine triazole compounds of formula I may be used in mixtures,applied simultaneously or sequentially, alone or with other compounds toenhance plant vigor (e.g. to grow a better root system, to betterwithstand stressful growing conditions). Such other compounds are, forexample, compounds that modulate plant ethylene receptors, most notably1-methylcyclopropene (also known as 1-MCP). Furthermore, such moleculesmay be used during times when pest activity is low, such as before theplants that are growing begin to produce valuable agriculturalcommodities. Such times include the early planting season when pestpressure is usually low.

The pyridine triazole compounds of formula I can be applied to thefoliar and fruiting portions of plants to control pests. The moleculeswill either come in direct contact with the pest, or the pest willconsume the pesticide when eating leaf, fruit mass, or extracting sap,that contains the pesticide. The pyridine triazole compounds of formulaI can also be applied to the soil, and when applied in this manner, rootand stem feeding pests can be controlled. The roots can absorb amolecule taking it up into the foliar portions of the plant to controlabove ground chewing and sap feeding pests.

Generally, with baits, the baits are placed in the ground where, forexample, termites can come into contact with, and/or be attracted to,the bait. Baits can also be applied to a surface of a building,(horizontal, vertical, or slant surface) where, for example, ants,termites, cockroaches, and flies, can come into contact with, and/or beattracted to, the bait. Baits can comprise a pyridine triazole compoundsof formula I.

The pyridine triazole compounds of formula I can be encapsulated inside,or placed on the surface of a capsule. The size of the capsules canrange from nanometer size (about 100-900 nanometers in diameter) tomicrometer size (about 10-900 microns in diameter).

Because of the unique ability of the eggs of some pests to resistcertain pesticides, repeated applications of the pyridine triazolecompounds of formula I may be desirable to control newly emerged larvae.

Systemic movement of pesticides in plants may be utilized to controlpests on one portion of the plant by applying (for example by sprayingan area) the pyridine triazole compounds of formula I to a differentportion of the plant. For example, control of foliar-feeding insects canbe achieved by drip irrigation or furrow application, by treating thesoil with for example pre- or post-planting soil drench, or by treatingthe seeds of a plant before planting.

Seed treatment can be applied to all types of seeds, including thosefrom which plants genetically modified to express specialized traitswill germinate. Representative examples include those expressingproteins toxic to invertebrate pests, such as Bacillus thuringiensis orother insecticidal toxins, those expressing herbicide resistance, suchas “Roundup Ready” seed, or those with “stacked” foreign genesexpressing insecticidal toxins, herbicide resistance,nutrition-enhancement, drought resistance, or any other beneficialtraits. Furthermore, such seed treatments with the pyridine triazolecompounds of formula I may further enhance the ability of a plant tobetter withstand stressful growing conditions. This results in ahealthier, more vigorous plant, which can lead to higher yields atharvest time. Generally, about 1 gram of the pyridine triazole compoundsof formula I to about 500 grams per 100,000 seeds is expected to providegood benefits, amounts from about 10 grams to about 100 grams per100,000 seeds is expected to provide better benefits, and amounts fromabout 25 grams to about 75 grams per 100,000 seeds is expected toprovide even better benefits.

It should be readily apparent that the pyridine triazole compounds offormula I may be used on, in, or around plants genetically modified toexpress specialized traits, such as Bacillus thuringiensis or otherinsecticidal toxins, or those expressing herbicide resistance, or thosewith “stacked” foreign genes expressing insecticidal toxins, herbicideresistance, nutrition-enhancement, or any other beneficial traits.

The pyridine triazole compounds of formula I may be used for controllingendoparasites and ectoparasites in the veterinary medicine sector or inthe field of non-human animal keeping. The pyridine triazole compoundsof formula I are applied, such as by oral administration in the form of,for example, tablets, capsules, drinks, granules, by dermal applicationin the form of, for example, dipping, spraying, pouring on, spotting on,and dusting, and by parenteral administration in the form of, forexample, an injection.

The pyridine triazole compounds of formula I may also be employedadvantageously in livestock keeping, for example, cattle, sheep, pigs,chickens, and geese. They may also be employed advantageously in petssuch as, horses, dogs, and cats. Particular pests to control would befleas and ticks that are bothersome to such animals. Suitableformulations are administered orally to the animals with the drinkingwater or feed. The dosages and formulations that are suitable depend onthe species.

The pyridine triazole compounds of formula I may also be used forcontrolling parasitic worms, especially of the intestine, in the animalslisted above.

The pyridine triazole compounds of formula I may also be employed intherapeutic methods for human health care. Such methods include, but arelimited to, oral administration in the form of, for example, tablets,capsules, drinks, granules, and by dermal application.

Pests around the world have been migrating to new environments (for suchpest) and thereafter becoming a new invasive species in such newenvironment. The pyridine triazole compounds of formula I may also beused on such new invasive species to control them in such newenvironment.

The pyridine triazole compounds of formula I may also be used in an areawhere plants, such as crops, are growing (e.g. pre-planting, planting,pre-harvesting) and where there are low levels (even no actual presence)of pests that can commercially damage such plants. The use of suchmolecules in such area is to benefit the plants being grown in the area.Such benefits, may include, but are not limited to, improving the healthof a plant, improving the yield of a plant (e.g. increased biomassand/or increased content of valuable ingredients), improving the vigorof a plant (e.g. improved plant growth and/or greener leaves), improvingthe quality of a plant (e.g. improved content or composition of certainingredients), and improving the tolerance to abiotic and/or bioticstress of the plant.

Before a pesticide can be used or sold commercially, such pesticideundergoes lengthy evaluation processes by various governmentalauthorities (local, regional, state, national, and international).Voluminous data requirements are specified by regulatory authorities andmust be addressed through data generation and submission by the productregistrant or by a third party on the product registrant's behalf, oftenusing a computer with a connection to the World Wide Web. Thesegovernmental authorities then review such data and if a determination ofsafety is concluded, provide the potential user or seller with productregistration approval. Thereafter, in that locality where the productregistration is granted and supported, such user or seller may use orsell such pesticide.

A pyridine triazole compounds of formula I can be tested to determineits efficacy against pests. Furthermore, mode of action studies can beconducted to determine if said molecule has a different mode of actionthan other pesticides. Thereafter, such acquired data can bedisseminated, such as by the internet, to third parties.

The disclosed pesticidal composition comprising a pyridine triazolecompounds of formula I may be used to control a wide variety of pests.

As a non-limiting example, in one or more embodiments, the method of thepresent disclosure may be used to control one or more members ofLyriomiza sativae, Caliothrips phaseoli, Paratrioza cockerel, Spodopteraexigua, Myzus persicae, Nilaparvata lugens, Bemisia tabaci, and Myzuspersicae.

In additional embodiments, the method of the present disclosure may beused to control one or more members of at least one of PhylumArthropoda, Phylum Nematoda, Subphylum Chelicerata, Subphylum Myriapoda,Subphylum Hexapoda, Class Insecta, Class Arachnida, and Class Symphyla.In at least some embodiments, the method of the present disclosure maybe used to control one or more members of at least one of Class Insectaand Class Arachnida.

In further embodiments, the method of the present disclosure may be usedto control members of the Order Coleoptera (beetles) including, but notlimited to, Acanthoscelides spp. (weevils), Acanthoscelides obtectus(common bean weevil), Agrilus planipennis (emerald ash borer), Agriotesspp. (wireworms), Anoplophora glabripennis (Asian longhorned beetle),Anthonomus spp. (weevils), Anthonomus grandis (boll weevil), Aphidiusspp., Apion spp. (weevils), Apogonia spp. (grubs), Ataenius spretulus(Black Turfgrass Ataenius), Atomaria linearis (pygmy mangold beetle),Aulacophore spp., Bothynoderes punctiventris (beet root weevil), Bruchusspp. (weevils), Bruchus pisorum (pea weevil), Cacoesia spp.,Callosobruchus maculatus (southern cow pea weevil), Carpophilushemipteras (dried fruit beetle), Cassida vittata, Cerosterna spp.,Cerotoma spp. (chrysomelids), Cerotoma trifurcata (bean leaf beetle),Ceutorhynchus spp. (weevils), Ceutorhynchus assimilis (cabbage seedpodweevil), Ceutorhynchus napi (cabbage curculio), Chaetocnema spp.(chrysomelids), Colaspis spp. (soil beetles), Conoderus scalaris,Conoderus stigmosus, Conotrachelus nenuphar (plum curculio), Cotinusnitidis (Green June beetle), Crioceris asparagi (asparagus beetle),Cryptolestes ferrugineus (rusty grain beetle), Cryptolestes pusillus(flat grain beetle), Cryptolestes turcicus (Turkish grain beetle),Ctenicera spp. (wireworms), Curculio spp. (weevils), Cyclocephala spp.(grubs), Cylindrocpturus adspersus (sunflower stem weevil), Deporausmarginatus (mango leafcutting weevil), Dermestes lardarius (larderbeetle), Dermestes maculates (hide beetle), Diabrotica spp.(chrysomelids), Epilachna varivestis (Mexican bean beetle), Faustinuscubae, Hylobius pales (pales weevil), Hypera spp. (weevils), Hyperapostica (alfalfa weevil), Hyperdoes spp. (Hyperodes weevil),Hypothenemus hampei (coffee berry beetle), Ips spp. (engravers),Lasioderma serricorne (cigarette beetle), Leptinotarsa decemlineata(Colorado potato beetle), Liogenys fuscus, Liogenys suturalis,Lissorhoptrus oryzophilus (rice water weevil), Lyctus spp. (woodbeetles/powder post beetles), Maecolaspis joliveti, Megascelis spp.,Melanotus communis, Meligethes spp., Meligethes aeneus (blossom beetle),Melolontha melolontha (common European cockchafer), Oberea brevis,Oberea linearis, Oryctes rhinoceros (date palm beetle), Oryzaephilusmercator (merchant grain beetle), Oryzaephilus surinamensis (sawtoothedgrain beetle), Otiorhynchus spp. (weevils), Oulema melanopus (cerealleaf beetle), Oulema oryzae, Pantomorus spp. (weevils), Phyllophaga spp.(May/June beetle), Phyllophaga cuyabana (chrysomelids), Phynchites spp.,Popillia japonica (Japanese beetle), Prostephanus truncates (largergrain borer), Rhizopertha dominica (lesser grain borer), Rhizotrogusspp. (European chafer), Rhynchophorus spp. (weevils), Scolytus spp.(wood beetles), Shenophorus spp. (Billbug), Sitona lineatus (pea leafweevil), Sitophilus spp. (grain weevils), Sitophilus granaries (granaryweevil), Sitophilus oryzae (rice weevil), Stegobium paniceum (drugstorebeetle), Tribolium spp. (flour beetles), Tribolium castaneum (red flourbeetle), Tribolium confusum (confused flour beetle), Trogodermavariabile (warehouse beetle), and Zabrus tenebioides.

In other embodiments, the method of the present disclosure may also beused to control members of the Order Dermaptera (earwigs).

In additional embodiments, the method of the present disclosure may beused to control members of the Order Dictyoptera (cockroaches)including, but is not limited to, Blattella germanica (Germancockroach), Blatta orientalis (oriental cockroach), Parcoblattapennylvanica, Periplaneta americana (American cockroach), Periplanetaaustraloasiae (Australian cockroach), Periplaneta brunnea (browncockroach), Periplaneta fuliginosa (smokybrown cockroach), Pyncoselussuninamensis (Surinam cockroach), and Supella longipalpa (brownbandedcockroach).

In further embodiments, the method of the present disclosure may be usedto control members of the Order Diptera (true flies) including, but isnot limited to, Aedes spp. (mosquitoes), Agromyza frontella (alfalfablotch leafminer), Agromyza spp. (leaf miner flies), Anastrepha spp.(fruit flies), Anastrepha suspensa (Caribbean fruit fly), Anopheles spp.(mosquitoes), Batrocera spp. (fruit flies), Bactrocera cucurbitae (melonfly), Bactrocera dorsalis (oriental fruit fly), Ceratitis spp. (fruitflies), Ceratitis capitata (Mediterranean fruit fly), Chrysops spp.(deer flies), Cochliomyia spp. (screwworms), Contarinia spp. (Gallmidges), Culex spp. (mosquitoes), Dasineura spp. (gall midges),Dasineura brassicae (cabbage gall midge), Delia spp., Delia platura(seedcorn maggot), Drosophila spp. (vinegar flies), Fannia spp. (filthflies), Fannia canicularis (little house fly), Fannia scalaris (latrinefly), Gasterophilus intestinalis (horse bot fly), Gracillia perseae,Haematobia irritans (horn fly), Hylemyia spp. (root maggots), Hypodermalineatum (common cattle grub), Liriomyza spp. (leafminer flies),Liriomyza brassica (serpentine leafminer), Melophagus ovinus (sheepked), Musca spp. (muscid flies), Musca autumnalis (face fly), Muscadomestica (house fly), Oestrus ovis (sheep bot fly), Oscinella frit(frit fly), Pegomyia betae (beet leafminer), Phorbia spp., Psila rosae(carrot rust fly), Rhagoletis cerasi (cherry fruit fly), Rhagoletispomonella (apple maggot), Sitodiplosis mosellana (orange wheat blossommidge), Stomoxys calcitrans (stable fly), Tabanus spp. (horse flies),and Tipula spp. (crane flies).

In other embodiments, the method of the present disclosure may be usedto control members of the Order Hemiptera (true bugs) including, but isnot limited to, Acrosternum hilare (green stink bug), Blissusleucopterus (chinch bug), Calocoris norvegicus (potato mirid), Cimexhemipterus (tropical bed bug), Cimex lectularius (bed bug), Dagbertusfasciatus, Dichelops furcatus, Dysdercus suturellus (cotton stainer),Edessa meditabunda, Eurygaster maura (cereal bug), Euschistus heros,Euschistus servus (brown stink bug), Helopeltis antonii, Helopeltistheivora (tea blight plantbug), Lagynotomus spp. (stink bugs),Leptocorisa oratorius, Leptocorisa varicornis, Lygus spp. (plant bugs),Lygus hesperus (western tarnished plant bug), Maconellicoccus hirsutus,Neurocolpus longirostris, Nezara viridula (southern green stink bug),Phytocoris spp. (plant bugs), Phytocoris californicus, Phytocorisrelativus, Piezodorus guildingi, Poecilocapsus lineatus (fourlined plantbug), Psallus vaccinicola, Pseudacysta perseae, Scaptocoris castanea,and Triatoma spp. (bloodsucking conenose bugs/kissing bugs).

In additional embodiments, the method of the present disclosure may beused to control members of the Order Homoptera (aphids, scales,whiteflies, leaflhoppers) including, but is not limited to,Acrythosiphon pisum (pea aphid), Adelges spp. (adelgids), Aleurodesproletella (cabbage whitefly), Aleurodicus disperses, Aleurothrixusfloccosus (woolly whitefly), Aluacaspis spp., Amrasca bigutellabigutella, Aphrophora spp. (leafhoppers), Aonidiella aurantii(California red scale), Aphis spp. (aphids), Aphis gossypii (cottonaphid), Aphis pomi (apple aphid), Aulacorthum solani (foxglove aphid),Bemisia spp. (whiteflies), Bemisia argentifolii, Bemisia tabaci(sweetpotato whitefly), Brachycolus noxius (Russian aphid),Brachycorynella asparagi (asparagus aphid), Brevennia rehi, Brevicorynebrassicae (cabbage aphid), Ceroplastes spp. (scales), Ceroplastes rubens(red wax scale), Chionaspis spp. (scales), Chrysomphalus spp. (scales),Coccus spp. (scales), Dysaphis plantaginea (rosy apple aphid), Empoascaspp. (leafhoppers), Eriosoma lanigerum (woolly apple aphid), Iceryapurchasi (cottony cushion scale), Idioscopus nitidulus (mangoleafhopper), Laodelphax striatellus (smaller brown planthopper),Lepidosaphes spp., Macrosiphum spp., Macrosiphum euphorbiae (potatoaphid), Macrosiphum granarium (English grain aphid), Macrosiphum rosae(rose aphid), Macrosteles quadrilineatus (aster leafhopper), Mahanarvafrimbiolata, Metopolophium dirhodum (rose grain aphid), Mictislongicornis, Myzus spp., Myzus persicae (green peach aphid), Nephotettixspp. (leafhoppers), Nephotettix cinctipes (green leafhopper),Nilaparvata lugens (brown planthopper), Parlatoria pergandii (chaffscale), Parlatoria ziziphi (ebony scale), Peregrinus maidis (corndelphacid), Philaenus spp. (spittlebugs), Phylloxera vitifoliae (grapephylloxera), Physokermes piceae (spruce bud scale), Planococcus spp.(mealybugs), Pseudococcus spp. (mealybugs), Pseudococcus brevipes (pineapple mealybug), Quadraspidiotus perniciosus (San Jose scale),Rhapalosiphum spp. (aphids), Rhapalosiphum maida (corn leaf aphid),Rhapalosiphum padi (oat bird-cherry aphid), Saissetia spp. (scales),Saissetia oleae (black scale), Schizaphis graminum (greenbug), Sitobionavenae (English grain aphid), Sogatella furcifera (white-backedplanthopper), Therioaphis spp. (aphids), Toumeyella spp. (scales),Toxoptera spp. (aphids), Trialeurodes spp. (whiteflies), Trialeurodesvaporariorum (greenhouse whitefly), Trialeurodes abutiloneus (bandedwingwhitefly), Unaspis spp. (scales), Unaspis yanonensis (arrowhead scale),and Zulia entreriana. In at least some embodiments, the method of thepresent disclosure may be used to control Myzus persicae.

In other embodiments, the method of the present disclosure may be usedto control members of the Order Hymenoptera (ants, wasps, and bees)including, but not limited to, Acromyrrmex spp., Athalia rosae, Attaspp. (leafcutting ants), Camponotus spp. (carpenter ants), Diprion spp.(sawflies), Formica spp. (ants), Iridomyrmex humilis (Argentine ant),Monomorium ssp., Monomorium minumum (little black ant), Monomoriumpharaonis (Pharaoh ant), Neodiprion spp. (sawflies), Pogonomyrmex spp.(harvester ants), Polistes spp. (paper wasps), Solenopsis spp. (fireants), Tapoinoma sessile (odorous house ant), Tetranomorium spp.(pavement ants), Vespula spp. (yellow jackets), and Xylocopa spp.(carpenter bees).

In certain embodiments, the method of the present disclosure may be usedto control members of the Order Isoptera (termites) including, but notlimited to, Coptotermes spp., Coptotermes curvignathus, Coptotermesfrenchii, Coptotermes formosanus (Formosan subterranean termite),Cornitermes spp. (nasute termites), Cryptotermes spp. (drywoodtermites), Heterotermes spp. (desert subterranean termites),Heterotermes aureus, Kalotermes spp. (drywood termites), Incistitermesspp. (drywood termites), Macrotermes spp. (fungus growing termites),Marginitermes spp. (drywood termites), Microcerotermes spp. (harvestertermites), Microtermes obesi, Procornitermes spp., Reticulitermes spp.(subterranean termites), Reticulitermes banyulensis, Reticulitermesgrassei, Reticulitermes flavipes (eastern subterranean termite),Reticulitermes hageni, Reticulitermes hesperus (western subterraneantermite), Reticulitermes santonensis, Reticulitermes speratus,Reticulitermes tibialis, Reticulitermes virginicus, Schedorhinotermesspp., and Zootermopsis spp. (rotten-wood termites).

In additional embodiments, the method of the present disclosure may beused to control members of the Order Lepidoptera (moths and butterflies)including, but not limited to, Achoea janata, Adoxophyes spp.,Adoxophyes orana, Agrotis spp. (cutworms), Agrotis ipsilon (blackcutworm), Alabama argillacea (cotton leafworm), Amorbia cuneana,Amyelosis transitella (navel orangeworm), Anacamptodes defectaria,Anarsia lineatella (peach twig borer), Anomis sabulifera (jute looper),Anticarsia gemmatalis (velvetbean caterpillar), Archips argyrospila(fruittree leafroller), Archips rosana (rose leaf roller), Argyrotaeniaspp. (tortricid moths), Argyrotaenia citrana (orange tortrix),Autographa gamma, Bonagota cranaodes, Borbo cinnara (rice leaf folder),Bucculatrix thurberiella (cotton leafperforator), Caloptilia spp. (leafminers), Capua reticulana, Carposina niponensis (peach fruit moth),Chilo spp., Chlumetia transversa (mango shoot borer), Choristoneurarosaceana (obliquebanded leafroller), Chrysodeixis spp., Cnaphalocerusmedinalis (grass leafroller), Colias spp., Conpomorpha cramerella,Cossus cossus (carpenter moth), Crambus spp. (Sod webworms),Cydiafunebrana (plum fruit moth), Cydia molesta (oriental fruit moth),Cydia nignicana (pea moth), Cydia pomonella (codling moth), Darnadiducta, Diaphania spp. (stem borers), Diatraea spp. (stalk borers),Diatraea saccharalis (sugarcane borer), Diatraea graniosella(southwester corn borer), Earias spp. (bollworms), Earias insulata(Egyptian bollworm), Earias vitella (rough northern bollworm),Ecdytopopha aurantianum, Elasmopalpus lignosellus (lesser cornstalkborer), Epiphysias postruttana (light brown apple moth), Ephestia spp.(flour moths), Ephestia cautella (almond moth), Ephestia elutella(tobbaco moth), Ephestia kuehniella (Mediterranean flour moth), Epimecesspp., Epinotia aporema, Erionota thrax (banana skipper), Eupoeciliaambiguella (grape berry moth), Euxoa auxiliaris (army cutworm), Feltiaspp. (cutworms), Gortyna spp. (stemborers), Grapholita molesta (orientalfruit moth), Hedylepta indicata (bean leaf webber), Helicoverpa spp.(noctuid moths), Helicoverpa armigera (cotton bollworm), Helicoverpa zea(bollworm/corn earworm), Heliothis spp. (noctuid moths), Heliothisvirescens (tobacco budworm), Hellula undalis (cabbage webworm),Indarbela spp. (root borers), Keiferia lycopersicella (tomato pinworm),Leucinodes orbonalis (eggplant fruit borer), Leucoptera malifoliella,Lithocollectis spp., Lobesia botrana (grape fruit moth), Loxagrotis spp.(noctuid moths), Loxagrotis albicosta (western bean cutworm), Lymantriadispar (gypsy moth), Lyonetia clerkella (apple leaf miner), Mahasenacorbetti (oil palm bagworm), Malacosoma spp. (tent caterpillars),Mamestra brassicae (cabbage armyworm), Maruca testulalis (bean podborer), Metisa plana (bagworm), Mythimna unipuncta (true armyworm),Neoleucinodes elegantalis (small tomato borer), Nymphula depunctalis(rice caseworm), Operophthera brumata (winter moth), Ostrinia nubilalis(European corn borer), Oxydia vesulia, Pandemis cerasana (common curranttortrix), Pandemis heparana (brown apple tortrix), Papilio demodocus,Pectinophora gossypiella (pink bollworm), Peridroma spp. (cutworms),Peridroma saucia (variegated cutworm), Perileucoptera coffeella (whitecoffee leafminer), Phthorimaea operculella (potato tuber moth),Phyllocnisitis citrella, Phyllonorycter spp. (leafminers), Pieris rapae(imported cabbageworm), Plathypena scabs, Plodia interpunctella (Indianmeal moth), Plutella xylostella (diamondback moth), Polychrosis viteana(grape berry moth), Prays endocarps, Prays oleae (olive moth),Pseudaletia spp. (noctuid moths), Pseudaletia unipunctata (armyworm),Pseudoplusia includens (soybean looper), Rachiplusia nu, Scirpophagaincertulas, Sesamia spp. (stemborers), Sesamia inferens (pink rice stemborer), Sesamia nonagrioides, Setora nitens, Sitotroga cerealella(Angoumois grain moth), Sparganothis pilleriana, Spodoptera spp.(armyworms), Spodoptera exigua (beet armyworm), Spodoptera fugiperda(fall armyworm), Spodoptera oridania (southern armyworm), Synanthedonspp. (root borers), Thecla basilides, Thermisia gemmatalis, Tineolabisselliella (webbing clothes moth), Trichoplusia ni (cabbage looper),Tuta absoluta, Yponomeuta spp., Zeuzera coffeae (red branch borer), andZeuzera pyrina (leopard moth). In at least some embodiments, the methodof the present disclosure may be used to control Spodoptera exigua.

The method of the present disclosure may be used to also control membersof the Order Mallophaga (chewing lice) including, but not limited to,Bovicola ovis (sheep biting louse), Menacanthus stramineus (chicken bodylouse), and Menopon gallinea (common hen louse).

In additional embodiments, the method of the present disclosure may beused to control members of the Order Orthoptera (grasshoppers, locusts,and crickets) including, but not limited to, Anabrus simplex (Mormoncricket), Gryllotalpidae (mole crickets), Locusta migratoria, Melanoplusspp. (grasshoppers), Microcentrum retinerve (angularwinged katydid),Pterophylla spp. (kaydids), chistocerca gregaria, Scudderia furcata(forktailed bush katydid), and Valanga nigricorni.

In other embodiments, the method of the present disclosure may be usedto control members of the Order Phthiraptera (sucking lice) including,but not limited to, Haematopinus spp. (cattle and hog lice), Linognathusovillus (sheep louse), Pediculus humanus capitis (human body louse),Pediculus humanus humanus (human body lice), and Pthirus pubis (crablouse).

In particular embodiments, the method of the present disclosure may beused to control members of the Order Siphonaptera (fleas) including, butnot limited to, Ctenocephalides canis (dog flea), Ctenocephalides felis(cat flea), and Pulex irritans (human flea).

In additional embodiments, the method of the present disclosure may beused to control members of the Order Thysanoptera (thrips) including,but not limited to, Frankliniella fusca (tobacco thrips), Frankliniellaoccidentalis (western flower thrips), Frankliniella shultzei,Frankliniella williamsi (corn thrips), Heliothrips haemorrhaidalis(greenhouse thrips), Riphiphorothrips cruentatus, Scirtothrips spp.,Scirtothrips citri (citrus thrips), Scirtothrips dorsalis (yellow teathrips), Taeniothrips rhopalantennalis, and Thrips spp.

The method of the present disclosure may be used to also control membersof the Order Thysanura (bristletails) including, but not limited to,Lepisma spp. (silverfish) and Thermobia spp. (firebrats).

In further embodiments, the method of the present disclosure may be usedto control members of the Order Acari (mites and ticks) including, butnot limited to, Acarapsis woodi (tracheal mite of honeybees), Acarusspp. (food mites), Acarus siro (grain mite), Aceria mangiferae (mangobud mite), Aculops spp., Aculops lycopersici (tomato russet mite),Aculops pelekasi, Aculus pelekassi, Aculus schlechtendali (apple rustmite), Amblyomma americanum (lone star tick), Boophilus spp. (ticks),Brevipalpus obovatus (privet mite), Brevipalpus phoenicis (red and blackflat mite), Demodex spp. (mange mites), Dermacentor spp. (hard ticks),Dermacentor variabilis (american dog tick), Dermatophagoidespteronyssinus (house dust mite), Eotetranycus spp., Eotetranychuscarpini (yellow spider mite), Epitimerus spp., Eriophyes spp., Ixodesspp. (ticks), Metatetranycus spp., Notoedres cati, Oligonychus spp.,Oligonychus coffee, Oligonychus ilicus (southern red mite), Panonychusspp., Panonychus citri (citrus red mite), Panonychus ulmi (European redmite), Phyllocoptruta oleivora (citrus rust mite), Polyphagotarsonemunlatus (broad mite), Rhipicephalus sanguineus (brown dog tick),Rhizoglyphus spp. (bulb mites), Sarcoptes scabiei (itch mite),Tegolophus perseaflorae, Tetranychus spp., Tetranychus urticae(twospotted spider mite), and Varroa destructor (honey bee mite).

In additional embodiments, the method of the present disclosure may beused to control members of the Order Nematoda (nematodes) including, butnot limited to, Aphelenchoides spp. (foliar nematodes), Belonolaimusspp. (sting nematodes), Criconemella spp. (ring nematodes), Dirofilariaimmitis (dog heartworm), Ditylenchus spp. (stem and bulb nematodes),Heterodera spp. (cyst nematodes), Heterodera zeae (corn cyst nematode),Hirschmanniella spp. (root nematodes), Hoplolaimus spp. (lancenematodes), Meloidogyne spp. (root knot nematodes), Meloidogyneincognita (root knot nematode), Onchocerca volvulus (hook-tail worm),Pratylenchus spp. (lesion nematodes), Radopholus spp. (burrowingnematodes), and Rotylenchus reniformis (kidney-shaped nematode).

In at least some embodiments, the method of the present disclosure maybe used to control at least one insect in one or more of the OrdersLepidoptera, Coleoptera, Homoptera, Hemiptera, Thysanoptera, Isoptera,Orthoptera, Diptera, Hymenoptera, and Siphonaptera, and at least onemite in the Order Acari.

DETAILED DESCRIPTION

Insecticidal Testing

Example A Bioassay for Green Peach Aphid (Myzus persicae) (GPA) (MYZUPE)

The green peach aphid (Myzus persicae) is the most significant aphidpest of peach trees, causing decreased growth, shriveling of the leaves,and the death of various tissues. It is also hazardous because it actsas a vector for the transport of plant viruses, such as potato virus Yand potato leafroll virus to members of the nightshade/potato familySolanaceae, and various mosaic viruses to many other food crops. GPAattacks such plants as broccoli, burdock, cabbage, carrot, cauliflower,daikon, eggplant, green beans, lettuce, macadamia, papaya, peppers,sweet potatoes, tomatoes, watercress, and zucchini, among other plants.GPA also attacks many ornamental crops such as carnation, chrysanthemum,flowering white cabbage, poinsettia, and roses. GPA has developedresistance to many pesticides.

Cabbage seedlings grown in 3-inch pots, with 2-3 small (3-5 cm) trueleaves, were used as test substrate. The seedlings were infested with20-50 GPA (wingless adult and nymph stages) one day prior to chemicalapplication. Four pots with individual seedlings were used for eachtreatment. Test compounds (2 mg) were dissolved in 2 mL ofacetone/methanol (1:1) solvent, forming stock solutions of 1000 ppm testcompound. The stock solutions were diluted 5× with 0.025% Tween 20 inH2O to obtain the solution at 200 ppm test compound. A hand-heldaspirator-type sprayer was used for spraying a solution to both sides ofcabbage leaves until runoff Reference plants (solvent check) weresprayed with the diluent only containing 20% by volume ofacetone/methanol (1:1) solvent. Treated plants were held in a holdingroom for three days at approximately 25° C. and ambient relativehumidity (RH) prior to grading. Evaluation was conducted by counting thenumber of live aphids per plant under a microscope. Percent control wasmeasured by using Abbott's correction formula (W. S. Abbott, “A Methodof Computing the Effectiveness of an Insecticide,” J. Econ. Entomol. 18(1925), pp. 265-267) as followsCorrected % Control=100*(X−Y)/X

where

X=No. of live aphids on solvent check plants and

Y=No. of live aphids on treated plants.

The results are indicated in the table entitled “TABLE 2. BiologicalData for Green Peach Aphid (GPA) (MYZUPE) and SweetpotatoWhitefly-crawler (WF) (BEMITA)” (see Table section).

Example B Insecticidal Test for Sweetpotato Whitefly-Crawler (WF)(Bemisia tabaci) (BEMITA) in Foliar Spray Assay

The sweetpotato whitefly (Bemisia tabaci) has been reported as a seriouspest of cultivated crops world-wide. It has an extremely wide host rangeattacking more than 500 species of plants from 63 plant families. Weedsoften serve as alternate hosts of crop pests. Direct feeding damage iscaused by the piercing and sucking sap from the foliage of plants. Thisfeeding causes weakening and early wilting of the plant and reduces theplant growth rate and yield. Indirect damage results by the accumulationof honeydew produced by the whiteflies. Honeydew serves as a substratefor the growth of black sooty mold on leaves and fruit reducingphotosynthesis and lessens the market value of the plant or yield.Damage is also caused when sweetpotato whitefly vectors plant viruses.The sweetpotato whitefly is considered the most common and importantwhitefly vector of plant viruses worldwide.

Cotton plants (Gossypium hirsutum) grown in 3-inch pots, with 1 small(4-5 cm) true leaves, were used as test substrate. The plants wereinfested with 200-400 whitefly eggs 4-5 days prior to chemicalapplication. Four pots with individual plants were used for eachtreatment. Test compounds (2 mg) were dissolved in 1 mL of acetonesolvent, forming stock solutions of 2000 ppm test compound. The stocksolutions were diluted 10× with 0.025% Tween 20 in H2O (diluents) toobtain the solution at 200 ppm test compound. A hand-held aspirator-typesprayer was used for spraying a solution to both sides of cotton leavesuntil runoff. Reference plants (solvent check) were sprayed with thediluent only containing 10% by volume of acetone solvent. Treated plantswere held in a holding room for 9 days at approximately 25° C. andambient relative humidity (RH) prior to grading. Evaluation wasconducted by counting the number of live 3-4 nymph stage per plant undera microscope. Percent control was measured by using Abbott's correctionformula (W. S. Abbott, “A Method of Computing the Effectiveness of anInsecticide,” J. Econ. Entomol. 18 (1925), pp. 265-267) as follows.Corrected % Control=100*(X−Y)/X

where

X=No. of live nymphs on solvent check plants and

Y=No. of live nymphs on treated plants.

The results are indicated in the table entitled “Table 2. BiologicalData for Green Peach Aphid (MYZUPE) and Sweetpotato Whitefly-crawler(WF) (BEMITA)” (see Table section).

Insecticidal Testing

TABLE 2 shows the pesticidal activities of the disclosed pesticidalcompounds against green peach aphid (GPA) and sweetpotatowhitefly-crawler (WF). The mortality efficiency of the pesticidalcompounds against GPA and WF insects was determined after treatment. Themortality efficiency of the disclosed pesticidal compounds against GPAand WF insects was rated as shown in TABLE 1.

TABLE 1 Mortality Rating for Green Peach Aphid and Whitefly % Control(or Mortality) Rating 80-100 A More than 0-Less than 80 B Not Tested CNo activity noticed in this bioassay D

TABLE 2 Biological Data for Green Peach Aphid (MYZUPE) and SweetpotatoWhitefly-crawler (BEMITA) Insect species GPA WF No. 200 ppm 200 ppm F1 BB F2 A B F3 A D F4 A A F5 A B F6 A B F7 A A F8 A A F9 A B F10 A B F11 BD F12 A A F13 A D

The following examples serve to explain embodiments of the presentinvention in more detail. These examples should not be construed asbeing exhaustive or exclusive as to the scope of this invention.

EXAMPLES

These examples are for illustration purposes and are not to be construedas limiting the disclosure to only the embodiments disclosed in theseexamples.

Starting materials, reagents, and solvents that were obtained fromcommercial sources were used without further purification. Anhydroussolvents were purchased as SURE/SEAL™ from Aldrich and were used asreceived. Melting points were obtained using a Thomas Hoover Unimeltcapillary melting point apparatus or an OptiMelt Automated Melting PointSystem from Stanford Research Systems and are uncorrected. Examplesusing “room temperature” were conducted in climate controlledlaboratories with a temperature ranging from about 20° C. to about 24°C. Chemical compounds were given their known names, named according tonaming programs within ISIS Draw, ChemDraw or ACD Name Pro. If suchprograms were unable to name the chemical compound, the chemicalcompound was named using conventional naming rules. ¹H NMR spectral datawere in ppm (δ) and were recorded at 300, 400 or 600 MHz. ¹³C NMRspectral data were in ppm (δ) and were recorded at 75, 100 or 150 MHz.¹⁹F NMR spectral data were in ppm (δ) and were recorded at 376 MHz,unless otherwise stated.

Example 1 Preparation of2-[1-(pyridin-3-yl)-1H-1,2,3-triazol-4-yl]-6-(trifluoromethyl) pyridineCompound F7

A stirred solution of3-(4-(tributylstannyl)-1H-1,2,3-triazol-1-yl)pyridine (0.396 g, 0.910mmol) (prepared according to Bioorganic & Medicinal Chemistry 2008,9817) in 1,4-dioxane (8.00 mL) was charged with2-bromo-6-(trifluoromethyl)pyridine (0.248 g, 1.10 mmol), CuI (0.0510 g,0.270 mmol), and Pd(PPh₃)₂Cl₂ (0.0630 g, 0.0900 mmol) sequentially atroom temperature (about 22° C.) under a nitrogen atmosphere. Thereaction mixture was evacuated and backfilled with nitrogen gas two orthree times, and was heated to reflux (about 100° C.) for 4 hours. Thereaction mixture was cooled and diluted with ethyl acetate (EtOAc, 20mL), shaken well with 5% aqueous potassium fluoride (KF) solution (3×50mL), and passed through a CELITE® bed. The organic layer was washed withbrine solution (2×25 mL), dried over anhydrous sodium sulfate (Na₂SO₄),and concentrated under reduced pressure. The crude residue was purifiedby flash column chromatography (0-50% EtOAc/hexanes with 1%triethylamine as coeluent) to afford the title compound F7 as a solid(0.085 g, 32% yield).

The following compounds were prepared according to the proceduresdescribes in Example 1:

2-Chloro-6-[1-(pyridin-3-yl)-1H-1,2,3-triazol-4-yl]pyridine (F10) wasisolated in 34% yield.

2-Methoxy-6-[1-(pyridin-3-yl)-1H-1,2,3-triazol-4-yl]pyridine (F5) wasisolated in 40% yield.

2-Bromo-6-[1-(pyridin-3-yl)-1H-1,2,3-triazol-4-yl]pyridine (F9) wasisolated in 32% yield.

2-[1-(Pyridin-3-yl)-1H-1,2,3-triazol-4-yl]-5-(trifluoromethyl)pyridine(F8) was isolated in 36% yield.

Example 2 Preparation of2-methyl-6-(1-(pyridin-3-yl)-1H-1,2,3-triazol-4-yl)pyridine Compound F12

A stirred solution of3-(4-(tributylstannyl)-1H-1,2,3-triazol-1-yl)pyridine (0.348 g, 0.800mmol) in 1,4-dioxane (10 mL) was charged with 2-bromo-6-methylpyridine(0.165 g, 0.960 mmol), CsF (0.243 g, 1.60 mmol), 4 Å molecular sieves(0.100 g), and[1,3-bis(2,6-diisopropylphenyl)-imidazol-2-ylidene]-(3-chloropyridyl)palladium(II)dichloride (Pd-PEPPSI-IPr) precatalyst (0.0200 g, 0.0300 mmol)successively at room temperature under a nitrogen atmosphere. Thereaction mixture was evacuated and backfilled with nitrogen gas two orthree times, and was heated at reflux for 4 hours. The reaction mixturewas cooled to room temperature, diluted with EtOAc (20 mL), shaken wellwith 5% aqueous KF solution (3×50 mL), and passed through a CELITE® bed.The organic layer was washed with brine solution (2×25 mL), dried overanhydrous Na₂SO₄, and concentrated under reduced pressure. The cruderesidue was purified by flash column chromatography (0-100%EtOAc/hexanes with 1% triethylamine as coeluent) to afford the compound(F12) as a solid (0.0820 g, 44%).

The following compound was prepared according to the proceduresdisclosed in Example 2:

5-Methyl-2-[1-(pyridin-3-yl)-1H-1,2,3-triazol-4-yl]pyridine (F4),isolated in 40% yield.

Example 3 Preparation of3-(4-(3-(trifluoromethoxy)phenyl)-1H-1,2,3-triazol-1-yl)pyridineCompound F6

A stirred solution of 3-(4-iodo-1H-1,2,3-triazol-1-yl)pyridine (0.15 g,0.55 mmol) in 1,4-dioxane (6.0 mL) and water (6.0 mL) was charged with(3-(trifluoromethoxy)phenyl)boronic acid (0.12 g, 0.60 mmol), Na₂CO₃ (29mg, 0.27 mmol), and Pd(PPh₃)₂Cl₂ (21 mg, 0.03 mmol) sequentially at roomtemperature under a nitrogen atmosphere. The reaction flask wasevacuated and backfilled with nitrogen gas two or three times, and washeated at reflux for 4 hours. The reaction mixture was diluted withwater (20 mL) and extracted with EtOAc (2×50 mL). The combined organiclayer was washed with brine solution (2×25 mL), dried over anhydrousNa₂SO₄, and concentrated under reduced pressure. The crude residue waspurified by flash column chromatography (0-100% EtOAc/hexanes with 1%triethylamine as coeluent) to afford the title compound (F6) as a solid(0.12 g, 65%).

The following compounds were prepared according to the proceduresdisclosed in Example 3:

3-[4-(2-Chlorophenyl)-1H-1,2,3-triazol-4-yl]pyridine (F1) was isolatedin 53% yield.

3-{4-[3-(Trifluoromethyl)phenyl]-1H-1,2,3-triazol-4-yl}pyridine (F13)was isolated in 71% yield.

3-{4-[3-(methylthio)phenyl]-1H-1,2,3-triazol-4-yl}pyridine (F3) wasisolated in 44% yield.

3-[4-(3-Chlorophenyl)-1H-1,2,3-triazol-4-yl]pyridine (F11) was isolatedin 56% yield.

5-[1-(Pyridin-3-yl)-1H-1,2,3-triazol-4-yl]-2-(trifluoromethyl)pyridine(F2) was isolated in 71% yield.

TABLE 3 shows non-limiting examples of the pyridine triazole compoundsof formula I. Compounds F1, F2, F3, F11, and F13 were prepared accordingto Example 3. Compounds F4, F6, and F12 were prepared according toExample 2. Compounds F5, F7, F8, F9, and F10 were prepared according toExample 1.

ESIMS No. Structure (m/z) ¹H NMR F1

Off- White Solid 257.0 ([M + H]⁺) (400 MHz, CDCl₃) δ 9.11 (s, 1H), 8.76(d, J = 4.0 Hz, 1H), 8.69 (s, 1H), 8.34 (dd, J = 8.0, 1.6 Hz, 1H),8.24-8.21 (m, 1H), 7.57-7.51 (m, 2H), 7.44 (t, J = 7.6 Hz, 1H), 7.35 (t,J = 8.0 Hz, 1H) F2

Off- White Solid 292 ([M + H]⁺) ¹H NMR (300 MHz, CDCl₃) δ 9.20 (d, J =2.4 Hz, 1H), 9.10 (d, J = 2.4 Hz, 1H), 8.78 (dd, J = 4.8, 1.2 Hz, 1H),8.50 (dd, J = 8.1, 1.2 Hz, 1H), 8.43 (s, 1H), 8.24-8.20 (m, 1H), 7.83(d, J = 8.1 Hz, 1H), 7.59-7.55 (m, 1H) F3

Light Brown Solid 269.0 ([M + H]⁺) ¹H NMR (300 MHz, CDCl₃) δ 9.07 (d, J= 2.4 Hz, 1H), 8.73 (d, J = 4.0 Hz, 1H), 8.25 (s, 1H), 8.23-8.19 (m,1H), 7.84 (s, 1H), 7.65 (d, J = 7.5 Hz, 1H), 7.56-7.51 (m, 1H), 7.39 (t,J = 7.5 Hz, 1H), 7.29 (s, 1H), 2.56 (s, 3H) F4

Off- White Solid 238.1 ([M + H]⁺) ¹H NMR (400 MHz, CDCl₃) δ 9.12 (d, J =2.4 Hz, 1H), 8.73 (dd, J = 4.8, 1.6 Hz, 1H), 8.61 (s, 1H), 8.46 (s, 1H),8.22-8.19 (m, 1H), 8.15 (d, J = 8.0 Hz, 1H), 7.64 (dd, J = 8.0, 1.2 Hz,1H), 7.54-7.51 (m, 1H), 2.40 (s, 3H) F5

Light Yellow Solid ESIMS m/z 254.1 ([M + H]⁺) ¹H NMR (400 MHz, CDCl₃) δ9.13 (d, J = 2.4 Hz, 1H), 8.76 (d, J = 4.0 Hz, 1H), 8.58 (s, 1H), 8.25(d, J = 8.4 Hz, 1H), 7.86 (d, J = 7.6 Hz, 1H), 7.73 (t, J = 7.6 Hz, 1H),7.57-7.54 (m, 1H), 6.77 (d, J = 8.4 Hz, 1H), 4.03 (s, 3H) F6

Light Yellow Solid ESIMS m/z 307 ([M + H]⁺) ¹H NMR (400 MHz, CDCl₃) δ9.08 (d, J = 2.4 Hz, 1H), 8.76 (d, J = 4.8 Hz, 1H), 8.29 (s, 1H),8.23-8.20 (m, 1H), 7.86 (d, J = 8.0 Hz, 1H), 7.80 (s, 1H), 7.57-7.50 (m,2H), 7.25 (s, 1H) F7

Light Yellow Solid ESIMS m/z 292.1 ([M + H]⁺) ¹H NMR (400 MHz, CDCl₃) δ9.15 (d, J = 2.4 Hz, 1H), 8.77- 8.76 (m, 1H), 8.75 (s, 1H), 8.45 (d, J =8.0 Hz, 1H), 8.23- 8.20 (m, 1H), 8.02 (t, J = 8.0 Hz, 1H), 7.67 (d, J =8.0 Hz, 1H), 7.57-7.53 (m, 1H) F8

Off- White Solid ESIMS m/z 292.0 ([M + H]⁺) ¹H NMR (400 MHz, CDCl₃) δ9.12 (d, J = 2.4 Hz, 1H), 8.88 (s, 1H), 8.76 (d, J = 4.0 Hz, 1H), 8.72(s, 1H), 8.40 (d, J = 8.0 Hz, 1H), 8.24-8.21 (m, 1H), 8.08 (dd, J = 8.4,2.0 Hz, 1H), 7.58-7.54 (m, 1H) F9

Off- White Solid 302/304 ([M + H]⁺) ¹H NMR (400 MHz, CDCl₃) δ 9.11 (d, J= 2.4 Hz, 1H), 8.75 (dd, J = 4.8 Hz, 1.2 Hz, 1H), 8.69 (s, 1H),8.23-8.18 (m, 2H), 7.68 (t, d, J = 8.0 Hz, 1H), 7.55-7.51 (m, 1H), 7.48-7.46 (m, 1H) F10

Off- White Solid 258.0 ([M + H]⁺) ¹H NMR (400 MHz, CDCl₃) δ 9.11 (d, J =2.4 Hz, 1H), 8.75 (dd, J = 4.8 Hz, 1.2 Hz, 1H), 8.69 (s, 1H), 8.21-8.18(m, 2H), 7.80 (t, d, J = 8.0 Hz, 1H), 7.55-7.52 (m, 1H), 7.33 (d, J =8.0 Hz, 1H) F11

Off- White Solid 257.11 ([M + H]⁺) ¹H NMR (400 MHz, CDCl₃) δ 9.07 (s,1H), 8.76 (d, J = 4.0 Hz, 1H), 8.27 (s, 1H), 8.23- 8.20 (m, 1H), 7.94(s, 1H), 7.83 (d, J = 7.2 Hz, 1H), 7.57- 7.54 (m, 1H), 7.45-7.36 (m, 2H)F12

Off- White Solid 238.1 ([M + H]⁺) ¹H NMR (300 MHz, CDCl₃) δ 9.12 (d, J =2.4 Hz, 1H), 8.73 (dd, J = 4.8, 1.2 Hz, 1H), 8.66 (s, 1H), 8.24-8.21 (m,1H), 8.05 (d, J = 11.4 Hz, 1H), 7.71 (t, d, J = 7.8 Hz, 1H), 7.55- 7.51(m, 1H), 7.15 (d, J = 7.8 Hz, 1H), 2.60 (s, 3H) F13

Off- White Solid 291.0 ([M + H]⁺) ¹H NMR (400 MHz, CDCl₃) δ 9.10 (s,1H), 8.77 (s, 1H), 8.34 (s, 1H), 8.24-8.22 (m, 1H), 8.18 (s, 1H), 8.15(d, J = 7.6 Hz, 1H), 7.68-7.55 (m, 3H)

Example 4 Preparation of2-(6-(1-(pyridin-3-yl)-1H-1,2,3-triazol-4-yl)pyridin-2-yl)pyrimidineCompound P1

To (1-(pyridin-3-yl)-1H-1,2,3-triazol-4-yl)boronic acid in anappropriate reaction vessel may be added2-(6-bromopyridin-2-yl)pyrimidine (from about 1 eq to about 1.5 eq) in asolvent, such as 1,4-dioxane at a concentration between about 0.01 M toabout 1 M. Then, a base such as Na₂CO₃ (from about 1 eq to about 5 eq)and a catalyst such as Pd(PPh₃)₄ (from about 0.01 eq to about 0.5 eq)may be added. The reaction may be stirred at a temperature of from about50° C. to about 150° C. until the reaction was determined to becompleted. Following completion of the reaction, the product may beobtained using standard organic chemistry techniques of workup andpurification.

The following compounds may be prepared according to the proceduresdisclosed in Example 4: P1, P2, and P3.

While this invention has been described in certain embodiments, thepresent invention can be further modified within the spirit and scope ofthis disclosure. This application is therefore intended to cover anyvariations, uses, or adaptations of the invention using its generalprinciples. Further, this application is intended to cover suchdepartures from the present disclosure as come within known or customarypractice in the art to which this invention pertains and which fallwithin the limits of the appended claims.

We claim:
 1. A pesticidal composition, comprising a pyridine triazolecompound of formula I, or any agriculturally acceptable salt thereof:

wherein: (a) R₁, R₂, and R₄ are independently hydrogen, F, Cl, Br, I,substituted or unsubstituted C₁-C₆ alkyl, or substituted orunsubstituted C₁-C₆ haloalkyl, wherein each R₁, R₂, and R₄, whensubstituted, has one or more substituents selected from F, Cl, Br, I,CN, NO₂, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₁-C₆ haloalkyl, C₃-C₁₀ cycloalkyl,or C₃-C₁₀ halocycloalkyl, where each of which is unsubstituted orsubstituted with R₁₁; (b) R₃ is hydrogen, F, Cl, Br, I, CN, NO₂,substituted or unsubstituted C₁-C₆ alkyl, substituted or unsubstitutedC₂-C₆ alkenyl, substituted or unsubstituted C₁-C₆ alkoxy, substituted orunsubstituted C₃-C₁₀ cycloalkyl, substituted or unsubstituted C₁-C₆haloalkyl, substituted or unsubstituted C₆-C₂₀ aryl, substituted orunsubstituted C₁-C₂₀ heterocyclyl, OR₁₁, C(═X₁)R₁₁, C(═X₁)R₁₁,C(═X₁)N(R₁₁)₂, N(R₁₁)₂, N(R₁₁)C(═X₁)R₁₁, SR₁₁, S(O),OR₁₁, orR₁₁S(O)_(n)R₁₁, wherein R₃, when substituted, has one or moresubstituents selected from F, Cl, Br, I, CN, NO₂, C₁-C₆ alkyl, C₂-C₆alkenyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₁-C₆ haloalkyloxy, C₂-C₆haloalkenyloxy, C₃-C₁₀ cycloalkyl, C₃-C₁₀ cycloalkenyl, C₃-C₁₀halocycloalkyl, C₃-C₁₀ halocycloalkenyl, OR₁₁, S(O)_(n)OR₁₁, C₆-C₂₀aryl, or C₁-C₂₀ heterocyclyl, wherein each of which is unsubstituted orsubstituted with R₁₁; (c) R₅ is hydrogen, F, Cl, Br, I, CN, NO₂,substituted or unsubstituted C₁-C₆ alkyl, substituted or unsubstitutedC₂-C₆ alkenyl, substituted or unsubstituted C₁-C₆ alkoxy, C₃-C₁₀cycloalkyl, substituted or unsubstituted C₆-C₂₀ aryl, substituted orunsubstituted C₁-C₂₀ heterocyclyl, OR₁₁, C(═X₁)R₁₁, C(═X₁)OR₁₁,C(═X₁)N(R₁₁)₂, N(R₁₁)₂, N(R₁₁)C(═X₁)R₁₁, SR₁₁, S(O)_(n)OR₁₁, orR₁₁S(O)_(n)R₁₁, wherein R₅, when substituted, has one or moresubstituents selected from F, Cl, Br, I, CN, NO₂, C₁-C₆ alkyl, C₂-C₆alkenyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl, C₁-C₆ haloalkyloxy, C₂-C₆haloalkenyloxy, C₃-C₁₀ cycloalkyl, C₃-C₁₀ cycloalkenyl, C₃-C₁₀halocycloalkyl, C₃-C₁₀ halocycloalkenyl, OR₁₁, S(O)_(n)OR₁₁, C₆-C₂₀aryl, or C₁-C₂₀ heterocyclyl, wherein each of which is unsubstituted orsubstituted with R₁₁; (d) Z is Z₁, Z₂, Z₃, Z₄, Z₅, Z₆, Z₇ or Z₈;

(e) R₆ is hydrogen, F, Cl, Br, I, CN, NO₂, OR₁₁, substituted orunsubstituted C₁-C₆ alkyl, substituted or unsubstituted C₂-C₆ alkenyl,substituted or unsubstituted C₁-C₆ alkoxy, substituted or unsubstitutedC₃-C₁₀ cycloalkyl, substituted or unsubstituted C₃-C₁₀ halocycloalkylsubstituted or unsubstituted C₃-C₁₀ cycloalkenyl, substituted orunsubstituted C₆-C₂₀ aryl, substituted or unsubstituted C₁-C₂₀heterocyclyl, C(═X₁)R₁₁, C(═X₁)OR₁₁, C(═X₁)N(R₁)₂, N(R₁₁)₂,N(R₁₁)C(═X₁)R₁₁, SR₁₁, S(O)_(n)OR₁₁, or R₁₁S(0)_(n)R₁₁, wherein R₆, whensubstituted, has one or more substituents selected from F, Cl, Br, I,CN, NO₂, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl,C₁-C₆ haloalkyloxy, C₂-C₆ haloalkenyloxy, C₃-C₁₀ cycloalkyl, C₃-C₁₀cycloalkenyl, C₃-C₁₀ halocycloalkyl, C₃-C₁₀ halocycloalkenyl, oxo, OR₁₁,S(O)_(n)R₁₁, C₆-C₂₀ aryl, or C₁-C₂₀ heterocyclyl, wherein each of whichis unsubstituted or substituted with R₁₁; (f) R₇ is selected fromhydrogen, F, Cl, Br, I, CN, NO₂, OR₁₁, substituted or unsubstitutedC₁-C₆ alkyl, substituted or unsubstituted C₂-C₆ alkenyl, substituted orunsubstituted C₁-C₆ alkoxy, substituted or unsubstituted C₃-C₁₀cycloalkyl, substituted or unsubstituted C₃-C₁₀ halocycloalkylsubstituted or unsubstituted C₃-C₁₀ cycloalkenyl, substituted orunsubstituted C₆-C₂₀ aryl, substituted or unsubstituted C₁-C₂₀heterocyclyl, C(═X₁)R₁₁, C(═X₁)OR₁₁, C(═X₁)N(R₁₁)₂, N(R₁₁)₂,N(R₁₁)C(═X₁)R₁₁, SR₁₁, S(O)_(n)OR₁₁, or R₁₁S(O)_(n)R₁₁, wherein R₇, whensubstituted, has one or more substituents selected from F, Cl, Br, I,CN, NO₂, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl,C₁-C₆ haloalkyloxy, C₂-C₆ haloalkenyloxy, C₃-C₁₀ cycloalkyl, C₃-C₁₀cycloalkenyl, C₃-C₁₀ halocycloalkyl, C₃-C₁₀ halocycloalkenyl, oxo, OR₁₁,S(O)_(n)R₁₁, C₆-C₂₀ aryl, or C₁-C₂₀ heterocyclyl, wherein each of whichis unsubstituted or substituted with R₁₁; (g) R₈ is hydrogen, F, Cl, Br,I, CN, NO₂, OR₁₁, substituted or unsubstituted C₁-C₆ alkyl, substitutedor unsubstituted C₂-C₆ alkenyl, substituted or unsubstituted C₁-C₆alkoxy, substituted or unsubstituted C₃-C₁₀ cycloalkyl, substituted orunsubstituted C₃-C₁₀ halocycloalkyl substituted or unsubstituted C₃-C₁₀cycloalkenyl, substituted or unsubstituted C₆-C₂₀ aryl, substituted orunsubstituted C₁-C₂₀ heterocyclyl, C(═X₁)R₁₁, C(═X₁)OR₁₁, C(═X₁)N(R₁₁)₂,N(R₁₁)₂, N(R₁₁)C(═X₁)R₁₁, SR₁₁, S(O)_(n)OR₁₁, or R₁₁S(O)_(n)R₁₁, whereinR₈, when substituted, has one or more substituents selected from F, Cl,Br, I, CN, NO₂, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₁-C₆ haloalkyl, C₂-C₆haloalkenyl, C₁-C₆ haloalkyloxy, C₂-C₆ haloalkenyloxy, C₃-C₁₀cycloalkyl, C₃-C₁₀ cycloalkenyl, C₃-C₁₀ halocycloalkyl, C₃-C₁₀halocycloalkenyl, oxo, OR₁₁, S(O)_(n)R₁₁, C₆-C₂₀ aryl, or C₁-C₂₀heterocyclyl, wherein each of which is unsubstituted or substituted withR₁₁; (h) R₉ is hydrogen, F, Cl, Br, I, CN, NO₂, —OR₁₁, substituted orunsubstituted C₁-C₆ alkyl, substituted or unsubstituted C₂-C₆ alkenyl,substituted or unsubstituted C₁-C₆ alkoxy, substituted or unsubstitutedC₃-C₁₀ cycloalkyl, substituted or unsubstituted C₃-C₁₀ halocycloalkyl,substituted or unsubstituted C₃-C₁₀ cycloalkenyl, substituted orunsubstituted C₆-C₂₀ aryl, substituted or unsubstituted C₁-C₂₀heterocyclyl, C(═X₁)R₁₁, C(═X₁)OR₁₁, C(═X₁)N(R₁₁)₂, N(R₁₁)₂,N(R₁₁)C(═X₁)R₁₁, SR₁₁, S(O)_(n)OR₁₁, or R₁₁S(O)_(n)R₁₁, wherein R₉, whensubstituted, has one or more substituents selected from F, Cl, Br, I,CN, NO₂, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl,C₁-C₆ haloalkyloxy, C₂-C₆ haloalkenyloxy, C₃-C₁₀ cycloalkyl, C₃-C₁₀cycloalkenyl, C₃-C₁₀ halocycloalkyl, C₃-C₁₀ halocycloalkenyl, oxo, OR₁₁,S(O)_(n)R₁₁, C₆-C₂₀ aryl, or C₁-C₂₀ heterocyclyl, wherein each of whichis unsubstituted or substituted with R₁₁; (i) R₁₀ is selected fromhydrogen, F, Cl, Br, I, CN, NO₂, OR₁₁, substituted or unsubstitutedC₁-C₆ alkyl, substituted or unsubstituted C₂-C₆ alkenyl, substituted orunsubstituted C₁-C₆ alkoxy, substituted or unsubstituted C₃-C₁₀cycloalkyl, substituted or unsubstituted C₃-C₁₀ halocycloalkylsubstituted or unsubstituted C₃-C₁₀ cycloalkenyl, substituted orunsubstituted C₆-C₂₀ aryl, substituted or unsubstituted C₁-C₂₀heterocyclyl,C(═X₁)R₁₁, C(═X₁)OR₁₁, C(═X₁)N(R₁₁)₂, N(R₁₁)₂,N(R₁₁)C(═X₁)R₁₁, SR₁₁, S(O)_(n)OR₁₁, or R₁₁S(O)_(n)R₁₁, wherein R₁₀,when substituted, has one or more substituents selected from F, Cl, Br,I, CN, NO₂, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₁-C₆ haloalkyl, C₂-C₆haloalkenyl, C₁-C₆ haloalkyloxy, C₂-C₆ haloalkenyloxy, C₃-C₁₀cycloalkyl, C₃-C₁₀ cycloalkenyl, C₃-C₁₀ halocycloalkyl, C₃-C₁₀halocycloalkenyl, oxo, OR₁₁, S(O)_(n)R₁₁, C₆-C₂₀ aryl, or C₁-C₂₀heterocyclyl, wherein each of which is unsubstituted or substituted withR_(11;) (j) R₁₁ is hydrogen, F, Cl, Br, I, CN, NO₂, substituted orunsubstituted C₁-C₆ alkyl, substituted or unsubstituted C₂-C₆ alkenyl,substituted or unsubstituted C₁-C₆ alkoxy, substituted or unsubstitutedC₂-C₆ alkenyloxy, substituted or unsubstituted C₃-C₁₀ cycloalkyl,substituted or unsubstituted C₃-C₁₀ cycloalkenyl, substituted orunsubstituted C₆-C₂₀ aryl, substituted or unsubstituted C₁-C₂₀heterocyclyl, substituted or unsubstituted S(O)_(n)C₁-C₆ alkyl, orsubstituted or unsubstituted N(C₁-C₆ alkyl)₂, wherein R₁₁, whensubstituted, has one or more substituents selected from F, Cl, Br, I,CN, NO₂, C₁-C₆ alkyl, C₂-C₆ alkenyl, C₁-C₆ haloalkyl, C₂-C₆ haloalkenyl,C₁-C₆ haloalkyloxy, C₂-C₆ haloalkenyloxy, C₃-C₁₀ cycloalkyl, C₃-C₁₀cycloalkenyl, C₃-C₁₀ halocycloalkyl, C₃-C₁₀ halocycloalkenyl, OC₁-C₆alkyl, OC₁-C₆ haloalkyl, S(O)_(n)C₁-C₆alkyl, S(O)_(n)OC₁-C₆ alkyl,C₆-C₂₀ aryl, or C₁-C₂₀ heterocyclyl; (k) X₁=O or S; (l) n is 0, 1, or 2;(m) x is 0 or 1; and (n) with the following provisos: (1) that when Z isZ₁, then at least one of R₆ and R₁₀ is not hydrogen,

(2) that when Z is Z₂, then at least two of R₆, R₇ and R₈ are nothydrogen,

(3) that when Z is Z₃, then at least one of R₇ and R₈ is not hydrogen,

(4) that when Z is Z₅, then at least one of R₈ and R₉ is not hydrogen,

(5) that when Z is Z₈, then at least one of R₆ and R₇ is not hydrogen.


2. A composition according to claim 1, wherein R₁, R₂, and R₄ are H. 3.A composition according to claim 1, wherein R₃ is selected from H, F,Cl, Br, or I.
 4. A composition according to claim 1, wherein R₅ ishydrogen.
 5. A composition according to claim 1, wherein Z is Z₄, Z₆, orZ₇.
 6. A composition according to claim 1, wherein Z is Z₅, and whereinR₆ and R₇ both simultaneously are hydrogen, or substituted orunsubstituted C₁-C₆ haloalkyl.
 7. The composition of claim 1, furthercomprising: (a) one or more compounds having acaricidal, algicidal,avicidal, bactericidal, fungicidal, herbicidal, insecticidal,molluscicidal, nematicidal, rodenticidal, or virucidal properties; or(b) one or more compounds that are antifeedants, bird repellents,chemosterilants, herbicide safeners, insect attractants, insectrepellents, mammal repellents, mating disrupters, plant activators,plant growth regulators, or synergists; or (c) both (a) and (b).
 8. Thecomposition of claim 1, further comprising one or more compoundsselected from: (3-ethoxypropyl)mercury bromide, 1,2-dichloropropane,1,3-dichloropropene, 1-methylcyclopropene, 1-naphthol,2-(octylthio)ethanol, 2,3,5-tri-iodobenzoic acid, 2,3,6-TBA,2,3,6-TBA-dimethylammonium, 2,3,6-TBA-lithium, 2,3,6-TBA-potassium,2,3,6-TBA-sodium, 2,4,5-T, 2,4,5-T-2-butoxypropyl, 2,4,5-T-2-ethylhexyl,2,4,5-T-3-butoxypropyl, 2,4,5-TB, 2,4,5-T-butometyl, 2,4,5-T-butotyl,2,4,5-T-butyl, 2,4,5-T-isobutyl, 2,4,5-T-isoctyl, 2,4,5-T-isopropyl,2,4,5-T-methyl, 2,4,5-T-pentyl, 2,4,5-T-sodium,2,4,5-T-triethylammonium, 2,4,5-T-trolamine, 2,4-D,2,4-D-2-butoxypropyl, 2,4-D-2-ethylhexyl, 2,4-D-3-butoxypropyl,2,4-D-ammonium, 2,4-DB, 2,4-DB-butyl, 2,4-DB-dimethylammonium,2,4-DB-isoctyl, 2,4-DB-potassium, 2,4-DB-sodium, 2,4-D-butotyl,2,4-D-butyl, 2,4-D-diethylammonium, 2,4-D-dimethylammonium,2,4-D-diolamine, 2,4-D-dodecylammonium, 2,4-DEB, 2,4-DEP, 2,4-D-ethyl,2,4-D-heptylammonium, 2,4-D-isobutyl, 2,4-D-isoctyl, 2,4-D-isopropyl,2,4-D-isopropylammonium, 2,4-D-lithium, 2,4-D-meptyl, 2,4-D-methyl,2,4-D-octyl, 2,4-D-pentyl, 2,4-D-potassium, 2,4-D-propyl, 2,4-D-sodium,2,4-D-tefuryl, 2,4-D-tetradecylammonium, 2,4-D-triethylammonium,2,4-D-tris(2-hydroxypropyl)ammonium, 2,4-D-trolamine, 2iP,2-methoxyethylmercury chloride, 2-phenylphenol, 3,4-DA, 3,4-DB, 3,4-DP,4-aminopyridine, 4-CPA, 4-CPA-potassium, 4-CPA-sodium, 4-CPB, 4-CPP,4-hydroxyphenethyl alcohol, 8-hydroxyquinoline sulfate,8-phenylmercurioxyquinoline, abamectin, abscisic acid, ACC, acephate,acequinocyl, acetamiprid, acethion, acetochlor, acetophos, acetoprole,acibenzolar, acibenzolar-S-methyl, acifluorfen, acifluorfen-methyl,acifluorfen-sodium, aclonifen, acrep, acrinathrin, acrolein,acrylonitrile, acypetacs, acypetacs-copper, acypetacs-zinc, alachlor,alanycarb, albendazole, aldicarb, aldimorph, aldoxycarb, aldrin,allethrin, allicin, allidochlor, allosamidin, alloxydim,alloxydim-sodium, allyl alcohol, allyxycarb, alorac, alpha-cypermethrin,alpha-endosulfan, ametoctradin, ametridione, ametryn, amibuzin,amicarbazone, amicarthiazol, amidithion, amidoflumet, amidosulfuron,aminocarb, aminocyclopyrachlor, aminocyclopyrachlor-methyl,aminocyclopyrachlor-potassium, aminopyralid, aminopyralid-potassium,aminopyralid-tris(2-hydroxypropyl)ammonium, amiprofos-methyl,amiprophos, amisulbrom, amiton, amiton oxalate, amitraz, amitrole,ammonium sulfamate, ammonium α-naphthaleneacetate, amobam, ampropylfos,anabasine, ancymidol, anilazine, anilofos, anisuron, anthraquinone,antu, apholate, aramite, arsenous oxide, asomate, aspirin, asulam,asulam-potassium, asulam-sodium, athidathion, atraton, atrazine,aureofungin, aviglycine, aviglycine hydrochloride, azaconazole,azadirachtin, azafenidin, azamethiphos, azimsulfuron, azinphos-ethyl,azinPhos-methyl, aziprotryne, azithiram, azobenzene, azocyclotin,azothoate, azoxystrobin, bachmedesh, barban, barium hexafluorosilicate,barium polysulfide, barthrin, BCPC, beflubutamid, benalaxyl,benalaxyl-M, benazolin, benazolin-dimethylammonium, benazolin-ethyl,benazolin-potassium, bencarbazone, benclothiaz, bendiocarb, benfluralin,benfuracarb, benfuresate, benodanil, benomyl, benoxacor, benoxafos,benquinox, bensulfuron, bensulfuron-methyl, bensulide, bensultap,bentaluron, bentazone, bentazone-sodium, benthiavalicarb,benthiavalicarb-isopropyl, benthiazole, bentranil, benzadox,benzadox-ammonium, benzalkonium chloride, benzamacril,benzamacril-isobutyl, benzamorf, benzfendizone, benzipram,benzobicyclon, benzofenap, benzofluor, benzohydroxamic acid,benzoximate, benzoylprop, benzoylprop-ethyl, benzthiazuron, benzylbenzoate, benzyladenine, berberine, berberine chloride, beta-cyfluthrin,beta-cypermethrin, bethoxazin, bicyclopyrone, bifenazate, bifenox,bifenthrin, bifujunzhi, bilanafos, bilanafos-sodium, binapacryl,bingqingxiao, bioallethrin, bioethanomethrin, biopermethrin,bioresmethrin, biphenyl, bisazir, bismerthiazol, bispyribac,bispyribac-sodium, bistrifluron, bitertanol, bithionol, bixafen,blasticidin-S, borax, Bordeaux mixture, boric acid, boscalid,brassinolide, brassinolide-ethyl, brevicomin, brodifacoum,brofenvalerate, brofluthrinate, bromacil, bromacil-lithium,bromacil-sodium, bromadiolone, bromethalin, bromethrin, bromfenvinfos,bromoacetamide, bromobonil, bromobutide, bromocyclen, bromo-DDT,bromofenoxim, bromophos, bromophos-ethyl, bromopropylate, bromothalonil,bromoxynil, bromoxynil butyrate, bromoxynil heptanoate, bromoxyniloctanoate, bromoxynil-potassium, brompyrazon, bromuconazole, bronopol,bucarpolate, bufencarb, buminafos, bupirimate, buprofezin, Burgundymixture, busulfan, butacarb, butachlor, butafenacil, butamifos,butathiofos, butenachlor, butethrin, buthidazole, buthiobate, buthiuron,butocarboxim, butonate, butopyronoxyl, butoxycarboxim, butralin,butroxydim, buturon, butylamine, butylate, cacodylic acid, cadusafos,cafenstrole, calcium arsenate, calcium chlorate, calcium cyanamide,calcium polysulfide, calvinphos, cambendichlor, camphechlor, camphor,captafol, captan, carbamorph, carbanolate, carbaryl, carbasulam,carbendazim, carbendazim benzenesulfonate, carbendazim sulfite,carbetamide, carbofuran, carbon disulfide, carbon tetrachloride,carbophenothion, carbosulfan, carboxazole, carboxide, carboxin,carfentrazone, carfentrazone-ethyl, carpropamid, cartap, cartaphydrochloride, carvacrol, carvone, CDEA, cellocidin, CEPC, ceralure,Cheshunt mixture, chinomethionat, chitosan, chlobenthiazone,chlomethoxyfen, chloralose, chloramben, chloramben-ammonium,chloramben-diolamine, chloramben-methyl, chloramben-methylammonium,chloramben-sodium, chloramine phosphorus, chloramphenicol,chloraniformethan, chloranil, chloranocryl, chlorantraniliprole,chlorazifop, chlorazifop-propargyl, chlorazine, chlorbenside,chlorbenzuron, chlorbicyclen, chlorbromuron, chlorbufam, chlordane,chlordecone, chlordimeform, chlordimeform hydrochloride,chlorempenthrin, chlorethoxyfos, chloreturon, chlorfenac,chlorfenac-ammonium, chlorfenac-sodium, chlorfenapyr, chlorfenazole,chlorfenethol, chlorfenprop, chlorfenson, chlorfensulphide,chlorfenvinphos, chlorfluazuron, chlorflurazole, chlorfluren,chlorfluren-methyl, chlorflurenol, chlorflurenol-methyl, chloridazon,chlorimuron, chlorimuron-ethyl, chlormephos, chlormequat, chlormequatchloride, chlomidine, chlornitrofen, chlorobenzilate,chlorodinitronaphthalenes, chloroform, chloromebuform, chloromethiuron,chloroneb, chlorophacinone, chlorophacinone-sodium, chloropicrin,chloropon, chloropropylate, chlorothalonil, chlorotoluron, chloroxuron,chloroxynil, chlorphonium, chlorphonium chloride, chlorphoxim,chlorprazophos, chlorprocarb, chlorpropham, chlorpyrifos,chlorpyrifos-methyl, chlorquinox, chlorsulfuron, chlorthal,chlorthal-dimethyl, chlorthal-monomethyl, chlorthiamid, chlorthiophos,chlozolinate, choline chloride, chromafenozide, cinerin I, cinerin II,cinerins, cinidon-ethyl, cinmethylin, cinosulfuron, ciobutide,cisanilide, cismethrin, clethodim, climbazole, cliodinate, clodinafop,clodinafop-propargyl, cloethocarb, clofencet, clofencet-potassium,clofentezine, clofibric acid, clofop, clofop-isobutyl, clomazone,clomeprop, cloprop, cloproxydim, elopyralid, clopyralid-methyl,clopyralid-olamine, clopyralid-potassium,clopyralid-tris(2-hydroxypropyl)ammonium, cloquintocet,cloquintocet-mexyl, cloransulam, cloransulam-methyl, closantel,clothianidin, clotrimazole, cloxyfonac, cloxyfonac-sodium, CMA,codlelure, colophonate, copper acetate, copper acetoarsenite, copperarsenate, copper carbonate, basic, copper hydroxide, copper naphthenate,copper oleate, copper oxychloride, copper silicate, copper sulfate,copper zinc chromate, coumachlor, coumafuryl, coumaphos, coumatetralyl,coumithoate, coumoxystrobin, CPMC, CPMF, CPPC, credazine, cresol,crimidine, crotamiton, crotoxyphos, crufomate, cryolite, cue-lure,cufraneb, cumyluron, cuprobam, cuprous oxide, curcumenol, cyanamide,cyanatryn, cyanazine, cyanofenphos, cyanophos, cyanthoate,cyantraniliprole, cyazofamid, cybutryne, cyclafuramid, cyclanilide,cyclethrin, cycloate, cycloheximide, cycloprate, cycloprothrin,cyclosulfamuron, cycloxydim, cycluron, cyenopyrafen, cyflufenamid,cyflumetofen, cyfluthrin, cyhalofop, cyhalofop-butyl, cyhalothrin,cyhexatin, cymiazole, cymiazole hydrochloride, cymoxanil, cyometrinil,cypendazole, cypermethrin, cyperquat, cyperquat chloride, cyphenothrin,cyprazine, cyprazole, cyproconazole, cyprodinil, cyprofuram, cypromid,cyprosulfamide, cyromazine, cythioate, daimuron, dalapon,dalapon-calcium, dalapon-magnesium, dalapon-sodium, daminozide,dayoutong, dazomet, dazomet-sodium, DBCP, d-camphor, DCIP, DCPTA, DDT,debacarb, decafentin, decarbofuran, dehydroacetic acid, delachlor,deltamethrin, demephion, demephion-O, demephion-S, demeton,demeton-methyl, demeton-O, demeton-O-methyl, demeton-S,demeton-S-methyl, demeton-S-methylsulphon, desmedipham, desmetryn,d-fanshiluquebingjuzhi, diafenthiuron, dialifos, di-allate, diamidafos,diatomaceous earth, diazinon, dibutyl phthalate, dibutyl succinate,dicamba, dicamba-diglycolamine, dicamba-dimethylammonium,dicamba-diolamine, dicamba-isopropylammonium, dicamba-methyl,dicamba-olamine, dicamba-potassium, dicamba-sodium, dicamba-trolamine,dicapthon, dichlobenil, dichlofenthion, dichlofluanid, dichlone,dichloralurea, dichlorbenzuron, dichlorflurenol, dichlorflurenol-methyl,dichlormate, dichlormid, dichlorophen, dichlorprop,dichlorprop-2-ethylhexyl, dichlorprop-butotyl,dichlorprop-dimethylammonium, dichlorprop-ethylammonium,dichlorprop-isoctyl, dichlorprop -methyl, dichlorprop-P,dichlorprop-P-2-ethylhexyl, dichlorprop-P-dimethylammonium,dichlorprop-potassium, dichlorprop-sodium, dichlorvos, dichlozoline,diclobutrazol, diclocymet, diclofop, diclofop-methyl, diclomezine,diclomezine-sodium, dicloran, diclosulam, dicofol, dicoumarol, dicresyl,dicrotophos, dicyclanil, dicyclonon, dieldrin, dienochlor, diethamquat,diethamquat dichloride, diethatyl, diethatyl-ethyl, diethofencarb,dietholate, diethyl pyrocarbonate, diethyltoluamide, difenacoum,difenoconazole, difenopenten, difenopenten-ethyl, difenoxuron,difenzoquat, difenzoquat metilsulfate, difethialone, diflovidazin,diflubenzuron, diflufenican, diflufenzopyr, diflufenzopyr-sodium,diflumetorim, dikegulac, dikegulac-sodium, dilor, dimatif, dimefluthrin,dimefox, dimefuron, dimepiperate, dimetachlone, dimetan, dimethacarb,dimethachlor, dimethametryn, dimethenamid, dimethenamid-P, dimethipin,dimethirimol, dimethoate, dimethomorph, dimethrin, dimethyl carbate,dimethyl phthalate, dimethylvinphos, dimetilan, dimexano, dimidazon,dimoxystrobin, dinex, dinex-diclexine, dingjunezuo, diniconazole,diniconazole-M, dinitramine, dinobuton, dinocap, dinocap-4, dinocap-6,dinocton, dinofenate, dinopenton, dinoprop, dinosaur, dinoseb, dinosebacetate, dinoseb-ammonium, dinoseb-diolamine, dinoseb-sodium,dinoseb-trolamine, dinosulfon, dinotefuran, dinoterb, dinoterb acetate,dinoterbon, diofenolan, dioxabenzofos, dioxacarb, dioxathion,diphacinone, diphacinone-sodium, diphenamid, diphenyl sulfone,diphenylamine, dipropalin, dipropetryn, dipyrithione, diquat, diquatdibromide, disparlure, disul, disulfiram, disulfoton, disul-sodium,ditalimfos, dithianon, dithicrofos, dithioether, dithiopyr, diuron,d-limonene, DMPA, DNOC, DNOC-ammonium, DNOC-potassium, DNOC-sodium,dodemorph, dodemorph acetate, dodemorph benzoate, dodicin, dodicinhydrochloride, dodicin-sodium, dodine, dofenapyn, dominicalure,doramectin, drazoxolon, DSMA, dufulin, EBEP, EBP, ecdysterone,edifenphos, eglinazine, eglinazine-ethyl, emamectin, emamectin benzoate,EMPC, empenthrin, endosulfan, endothal, endothal-diammonium,endothal-dipotassium, endothal-disodium, endothion, endrin,enestroburin, EPN, epocholeone, epofenonane, epoxiconazole,eprinomectin, epronaz, EPTC, erbon, ergocalciferol, erlujixiancaoan,esdépalléthrine, esfenvalerate, esprocarb, etacelasil, etaconazole,etaphos, etem, ethaboxam, ethachlor, ethaffluralin, ethametsulfuron,ethametsulfuron-methyl, ethaprochlor, ethephon, ethidimuron,ethiofencarb, ethiolate, ethion, ethiozin, ethiprole, ethirimol,ethoate-methyl, ethofumesate, ethohexadiol, ethoprophos, ethoxyfen,ethoxyfen-ethyl, ethoxyquin, ethoxysulfuron, ethychlozate, ethylformate, ethyl α-naphthaleneacetate, ethyl-DDD, ethylene, ethylenedibromide, ethylene dichloride, ethylene oxide, ethylicin, ethylmercury2,3-dihydroxypropyl mercaptide, ethylmercury acetate, ethylmercurybromide, ethylmercury chloride, ethylmercury phosphate, etinofen,etnipromid, etobenzanid, etofenprox, etoxazole, etridiazole, etrimfos,eugenol, EXD, famoxadone, famphur, fenamidone, fenaminosulf, fenamiphos,fenapanil, fenarimol, fenasulam, fenazaflor, fenazaquin, fenbuconazole,fenbutatin oxide, fenchlorazole, fenchlorazole-ethyl, fenchlorphos,fenclorim, fenethacarb, fenfluthrin, fenfuram, fenhexamid, fenitropan,fenitrothion, fenjuntong, fenobucarb, fenoprop, fenoprop-3-butoxypropyl,fenoprop-butometyl, fenoprop-butotyl, fenoprop-butyl, fenoprop-isoctyl,fenoprop-methyl, fenoprop-potassium, fenothiocarb, fenoxacrim,fenoxanil, fenoxaprop, fenoxaprop-ethyl, fenoxaprop-P,fenoxaprop-P-ethyl, fenoxasulfone, fenoxycarb, fenpiclonil,fenpirithrin, fenpropathrin, fenpropidin, fenpropimorph, fenpyrazamine,fenpyroximate, fenridazon, fenridazon-potassium, fenridazon-propyl,fenson, fensulfothion, fenteracol, fenthiaprop, fenthiaprop-ethyl,fenthion, fenthion-ethyl, fentin, fentin acetate, fentin chloride,fentin hydroxide, fentrazamide, fentrifanil, fenuron, fenuron TCA,fenvalerate, ferbam, ferimzone, ferrous sulfate, fipronil, flamprop,flamprop-isopropyl, flamprop-M, flamprop-methyl, flamprop-M-isopropyl,flamprop-M-methyl, flazasulfuron, flocoumafen, flometoquin, flonicamid,florasulam, fluacrypyrim, fluazifop, fluazifop-butyl, fluazifop-methyl,fluazifop-P, fluazifop-P-butyl, fluazinam, fluazolate, fluazuron,flubendiamide, flubenzimine, flucarbazone, flucarbazone-sodium,flucetosulfuron, fluchloralin, flucofuron, flucycloxuron, flucythrinate,fludioxonil, fluenetil, fluensulfone, flufenacet, flufenerim,flufenican, flufenoxuron, flufenprox, flufenpyr, flufenpyr-ethyl,flufiprole, flumethrin, flumetover, flumetralin, flumetsulam, flumezin,flumiclorac, flumiclorac-pentyl, flumioxazin, flumipropyn, flumorph,fluometuron, fluopicolide, fluopyram, fluorbenside, fluoridamid,fluoroacetamide, fluorodifen, fluoroglycofen, fluoroglycofen-ethyl,fluoroimide, fluoromidine, fluoronitrofen, fluothiuron, fluotrimazole,fluoxastrobin, flupoxam, flupropacil, flupropadine, flupropanate,flupropanate-sodium, flupyradifurone, flupyrsulfuron,flupyrsulfuron-methyl, flupyrsulfuron-methyl-sodium, fluquinconazole,flurazole, flurenol, flurenol-butyl, flurenol-methyl, fluridone,flurochloridone, fluroxypyr, fluroxypyr-butometyl, fluroxypyr-meptyl,flurprimidol, flursulamid, flurtamone, flusilazole, flusulfamide,fluthiacet, fluthiacet-methyl, flutianil, flutolanil, flutriafol,fluvalinate, fluxapyroxad, fluxofenim, folpet, fomesafen,fomesafen-sodium, fonofos, foramsulfuron, forchlorfenuron, formaldehyde,formetanate, formetanate hydrochloride, formothion, formparanate,formparanate hydrochloride, fosamine, fosamine-ammonium, fosetyl,fosetyl-aluminium, fosmethilan, fospirate, fosthiazate, fosthietan,frontalin, fuberidazole, fucaojing, fucaomi, funaihecaoling,fuphenthiourea, furalane, furalaxyl, furamethrin, furametpyr,furathiocarb, furcarbanil, furconazole, furconazole-cis, furethrin,furfural, furilazole, furmecyclox, furophanate, furyloxyfen,gamma-cyhalothrin, gamma-HCH, genit, gibberellic acid, gibberellins,gliftor, glufosinate, glufosinate-ammonium, glufosinate-P,glufosinate-P-ammonium, glufosinate-P-sodium, glyodin, glyoxime,glyphosate, glyphosate-diammonium, glyphosate-dimethylammonium,glyphosate-isopropylammonium, glyphosate-monoammonium, glyphosate-potassium, glypho sate- sesquisodium, glyphosate-trimesium,glyphosine, gossyplure, grandlure, griseofulvin, guazatine, guazatineacetates, halacrinate, halfenprox, halofenozide, halosafen,halosulfuron, halosulfuron-methyl, haloxydine, haloxyfop,haloxyfop-etotyl, haloxyfop-methyl, haloxyfop-P, haloxyfop-P-etotyl,haloxyfop-P-methyl, haloxyfop-sodium, HCH, hemel, hempa, HEOD,heptachlor, heptenophos, heptopargil, heterophos, hexachloroacetone,hexachlorobenzene, hexachlorobutadiene, hexachlorophene, hexaconazole,hexaflumuron, hexaflurate, hexalure, hexamide, hexazinone, hexylthiofos,hexythiazox, HHDN, holosulf, huancaiwo, huangcaoling, huanjunzuo,hydramethylnon, hydrargaphen, hydrated lime, hydrogen cyanide,hydroprene, hymexazol, hyquincarb, IAA, IBA, icaridin, imazalil,imazalil nitrate, imazalil sulfate, imazamethabenz,imazamethabenz-methyl, imazamox, imazamox-ammonium, imazapic,imazapic-ammonium, imazapyr, imazapyr-isopropylammonium, imazaquin,imazaquin-ammonium, imazaquin-methyl, imazaquin-sodium, imazethapyr,imazethapyr-ammonium, imazosulfuron, imibenconazole, imicyafos,imidacloprid, imidaclothiz, iminoctadine, iminoctadine triacetate,iminoctadine trialbesilate, imiprothrin, inabenfide, indanofan,indaziflam, indoxacarb, inezin, iodobonil, iodocarb, iodomethane,iodosulfuron, iodosulfuron-methyl, iodosulfuron-methyl-sodium,iofensulfuron, iofensulfuron-sodium, ioxynil, ioxynil octanoate,ioxynil-lithium, ioxynil-sodium, ipazine, ipconazole, ipfencarbazone,iprobenfos, iprodione, iprovalicarb, iprymidam, ipsdienol, ipsenol,IPSP, isamidofos, isazofos, isobenzan, isocarbamid, isocarbophos,isocil, isodrin, isofenphos, isofenphos-methyl, isolan, isomethiozin,isonoruron, isopolinate, isoprocarb, isopropalin, isoprothiolane,isoproturon, isopyrazam, isopyrimol, isothioate, isotianil, isouron,isovaledione, isoxaben, isoxachlortole, isoxadifen, isoxadifen-ethyl,isoxaflutole, isoxapyrifop, isoxathion, ivermectin, izopamfos,japonilure, japothrins, jasmolin I, jasmolin II, jasmonic acid,jiahuangchongzong, jiajizengxiaolin, jiaxiangjunzhi, jiecaowan,jiecaoxi, jodfenphos, juvenile hormone I, juvenile hormone II, juvenilehormone III, kadethrin, karbutilate, karetazan, karetazan-potassium,kasugamycin, kasugamycin hydrochloride, kejunlin, kelevan, ketospiradox,ketospiradox-potassium, kinetin, kinoprene, kresoxim-methyl, kuicaoxi,lactofen, lambda-cyhalothrin, latilure, lead arsenate, lenacil,lepimectin, leptophos, lindane, lineatin, linuron, lirimfos, litlure,looplure, lufenuron, lvdingjunzhi, lvxiancaolin, lythidathion, MAA,malathion, maleic hydrazide, malonoben, maltodextrin, MAMA, mancopper,mancozeb, mandipropamid, maneb, matrine, mazidox, MCPA,MCPA-2-ethylhexyl, MCPA-butotyl, MCPA-butyl, MCPA-dimethylammonium,MCPA-diolamine, MCPA-ethyl, MCPA-isobutyl, MCPA-isoctyl, MCPA-isopropyl,MCPA-methyl, MCPA-olamine, MCPA-potassium, MCPA-sodium, MCPA-thioethyl,MCPA-trolamine, MCPB, MCPB-ethyl, MCPB-methyl, MCPB-sodium, mebenil,mecarbam, mecarbinzid, mecarphon, mecoprop, mecoprop-2-ethylhexyl,mecoprop-dimethylammonium, mecoprop-diolamine, mecoprop-ethadyl,mecoprop-isoctyl, mecoprop-methyl, mecoprop-P, mecoprop-P-2-ethylhexyl,mecoprop-P-climethylammonium, mecoprop-P-isobutyl, mecoprop-potassium,mecoprop-P-potassium, mecoprop-sodium, mecoprop-trolamine, medimeform,medinoterb, medinoterb acetate, medlure, mefenacet, mefenpyr,mefenpyr-diethyl, mefluidide, mefluidide-diolamine,mefluidide-potassium, megatomoic acid, menazon, mepanipyrim,meperfluthrin, mephenate, mephosfolan, mepiquat, mepiquat chloride,mepiquat pentaborate, mepronil, meptyldinocap, mercuric chloride,mercuric oxide, mercurous chloride, merphos, mesoprazine, mesosulfuron,mesosulfuron-methyl, mesotrione, mesulfen, mesulfenfos, metaflumizone,metalaxyl, metalaxyl-M, metaldehyde, metam, metam-ammonium, metamifop,metamitron, metam-potassium, metam-sodium, metazachlor, metazosulfuron,metazoxolon, metconazole, metepa, metflurazon, methabenzthiazuron,methacrifos, methalpropalin, methamidophos, methasulfocarb, methazole,methfuroxam, methidathion, methiobencarb, methiocarb,methiopyrisulfuron, methiotepa, methiozolin, methiuron, methocrotophos,methometon, methomyl, methoprene, methoprotryne, methoquin-butyl,methothrin, methoxychlor, methoxyfenozide, methoxyphenone, methylapholate, methyl bromide, methyl eugenol, methyl iodide, methylisothiocyanate, methylacetophos, methylchloroform, methyldymron,methylene chloride, methylmercury benzoate, methylmercury dicyandiamide,methylmercury pentachlorophenoxide, methylneodecanamide, metiram,metobenzuron, metobromuron, metofluthrin, metolachlor, metolcarb,metominostrobin, metosulam, metoxadiazone, metoxuron, metrafenone,metribuzin, metsulfovax, metsulfuron, metsulfuron-methyl, mevinphos,mexacarbate, mieshuan, milbemectin, milbemycin oxime, milneb, mipafox,mirex, MNAF, moguchun, molinate, molosultap, monalide, monisouron,monochloroacetic acid, monocrotophos, monolinuron, monosulfuron,monosulfuron-ester, monuron, monuron TCA, morfamquat, morfamquatdichloride, moroxydine, moroxydine hydrochloride, morphothion, morzid,moxidectin, MSMA, muscalure, myclobutanil, myclozolin,N-(ethylmercury)-p-toluenesulphonanilide, nabam, naftalofos, naled,naphthalene, naphthaleneacetamide, naphthalic anhydride, naphthoxyaceticacids, naproanilide, napropamide, naptalam, naptalam-sodium, natamycin,neburon, niclosamide, niclosamide-olamine, nicosulfuron, nicotine,nifluridide, nipyraclofen, nitenpyram, nithiazine, nitralin, nitrapyrin,nitrilacarb, nitrofen, nitrofluorfen, nitrostyrene, nitrothal-isopropyl,norbormide, norflurazon, nornicotine, noruron, novaluron, noviflumuron,nuarimol, OCH, octachlorodipropyl ether, octhilinone, ofurace,omethoate, orbencarb, orfralure, ortho-dichlorobenzene, orthosulfamuron,oryctalure, orysastrobin, oryzalin, osthol, ostramone, oxabetrinil,oxadiargyl, oxadiazon, oxadixyl, oxamate, oxamyl, oxapyrazon,oxapyrazon-dimolamine, oxapyrazon-sodium, oxasulfuron, oxaziclomefone,oxine-copper, oxolinic acid, oxpoconazole, oxpoconazole fumarate,oxycarboxin, oxydemeton-methyl, oxydeprofos, oxydisulfoton, oxyfluorfen,oxymatrine, oxytetracycline, oxytetracycline hydrochloride,paclobutrazol, paichongding, para-dichlorobenzene, parafluron, paraquat,paraquat dichloride, paraquat dimetilsulfate, parathion,parathion-methyl, parinol, pebulate, pefurazoate, pelargonic acid,penconazole, pencycuron, pendimethalin, penflufen, penfluron,penoxsulam, pentachlorophenol, pentanochlor, penthiopyrad, pentmethrin,pentoxazone, perfluidone, permethrin, pethoxamid, phenamacril, phenazineoxide, phenisopham, phenkapton, phenmedipham, phenmedipham-ethyl,phenobenzuron, phenothrin, phenproxide, phenthoate, phenylmercuriurea,phenylmercury acetate, phenylmercury chloride, phenylmercury derivativeof pyrocatechol, phenylmercury nitrate, phenylmercury salicylate,phorate, phosacetim, phosalone, phosdiphen, phosfolan, phosfolan-methyl,phosglycin, phosmet, phosnichlor, phosphamidon, phosphine, phosphocarb,phosphorus, phostin, phoxim, phoxim-methyl, phthalide, picloram,picloram-2-ethylhexyl, picloram-isoctyl, picloram-methyl,picloram-olamine, picloram-potassium, picloram-triethylammonium,picloram-tris(2-hydroxypropyl)ammonium, picolinafen, picoxystrobin,pindone, pindone-sodium, pinoxaden, piperalin, piperonyl butoxide,piperonyl cyclonene, piperophos, piproctanyl, piproctanyl bromide,piprotal, pirimetaphos, pirimicarb, pirimioxyphos, pirimiphos-ethyl,pirimiphos-methyl, plifenate, polycarbamate, polyoxins, polyoxorim,polyoxorim-zinc, polythialan, potassium arsenite, potassium azide,potassium cyanate, potassium gibberellate, potassium naphthenate,potassium polysulfide, potassium thiocyanate, potassiumα-naphthaleneacetate, pp′-DDT, prallethrin, precocene I, precocene II,precocene III, pretilachlor, primidophos, primisulfuron,primisulfuron-methyl, probenazole, prochloraz, prochloraz-manganese,proclonol, procyazine, procymidone, prodiamine, profenofos, profluazol,profluralin, profluthrin, profoxydim, proglinazine, proglinazine-ethyl,prohexadione, prohexadione-calcium, prohydrojasmon, promacyl, promecarb,prometon, prometryn, promurit, propachlor, propamidine, propamidinedihydrochloride, propamocarb, propamocarb hydrochloride, propanil,propaphos, propaquizafop, propargite, proparthrin, propazine,propetamphos, propham, propiconazole, propineb, propisochlor, propoxur,propoxycarbazone, propoxycarbazone-sodium, propyl isome,propyrisulfuron, propyzamide, proquinazid, prosuler, prosulfalin,prosulfocarb, prosulfuron, prothidathion, prothiocarb, prothiocarbhydrochloride, prothioconazole, prothiofos, prothoate, protrifenbute,proxan, proxan-sodium, prynachlor, pydanon, pymetrozine, pyracarbolid,pyraclofos, pyraclonil, pyraclostrobin, pyraflufen, pyraflufen-ethyl,pyrafluprole, pyramat, pyrametostrobin, pyraoxystrobin, pyrasulfotole,pyrazolynate, pyrazophos, pyrazosulfuron, pyrazosulfuron-ethyl,pyrazothion, pyrazoxyfen, pyresmethrin, pyrethrin I, pyrethrin II,pyrethrins, pyribambenz-isopropyl, pyribambenz-propyl, pyribencarb,pyribenzoxim, pyributicarb, pyriclor, pyridaben, pyridafol, pyridalyl,pyridaphenthion, pyridate, pyridinitril, pyrifenox, pyrifluquinazon,pyriftalid, pyrimethanil, pyrimidifen, pyriminobac, pyriminobac-methyl,pyrimisulfan, pyrimitate, pyrinuron, pyriofenone, pyriprole,pyripropanol, pyriproxyfen, pyrithiobac, pyrithiobac-sodium, pyrolan,pyroquilon, pyroxasulfone, pyroxsulam, pyroxychlor, pyroxyfur, quassia,quinacetol, quinacetol sulfate, quinalphos, quinalphos-methyl,quinazamid, quinclorac, quinconazole, quinmerac, quinoclamine,quinonamid, quinothion, quinoxyfen, quintiofos, quintozene, quizalofop,quizalofop-ethyl, quizalofop-P, quizalofop-P-ethyl,quizalofop-P-tefuryl, quwenzhi, quyingding, rabenzazole, rafoxanide,rebemide, resmethrin, rhodethanil, rhodojaponin-III, ribavirin,rimsulfuron, rotenone, ryania, saflufenacil, saijunmao, saisentong,salicylanilide, sanguinarine, santonin, schradan, scilliroside,sebuthylazine, secbumeton, sedaxane, selamectin, semiamitraz,semiamitraz chloride, sesamex, sesamolin, sethoxydim, shuangjiaancaolin,siduron, siglure, silafluofen, silatrane, silica gel, silthiofam,simazine, simeconazole, simeton, simetryn, sintofen, SMA, S-metolachlor,sodium arsenite, sodium azide, sodium chlorate, sodium fluoride, sodiumfluoroacetate, sodium hexafluorosilicate, sodium naphthenate, sodiumorthophenylphenoxide, sodium pentachlorophenoxide, sodium polysulfide,sodium thiocyanate, sodium α-naphthaleneacetate, sophamide, spinetoram,spinosad, spirodiclofen, spiromesifen, spirotetramat, spiroxamine,streptomycin, streptomycin sesquisulfate, strychnine, sulcatol,sulcofuron, sulcofuron-sodium, sulcotrione, sulfallate, sulfentrazone,sulfiram, sulfluramid, sulfometuron, sulfometuron-methyl, sulfosulfuron,sulfotep, sulfoxaflor, sulfoxide, sulfoxime, sulfur, sulfuric acid,sulfuryl fluoride, sulglycapin, sulprofos, sultropen, swep,tau-fluvalinate, tavron, tazimcarb, TCA, TCA-ammonium, TCA-calcium,TCA-ethadyl, TCA-magnesium, TCA-sodium, TDE, tebuconazole, tebufenozide,tebufenpyrad, tebufloquin, tebupirimfos, tebutam, tebuthiuron,tecloftalam, tecnazene, tecoram, teflubenzuron, tefluthrin,tefuryltrione, tembotrione, temephos, tepa, TEPP, tepraloxydim,terallethrin, terbacil, terbucarb, terbuchlor, terbufos, terbumeton,terbuthylazine, terbutryn, tetcyclacis, tetrachloroethane,tetrachlorvinphos, tetraconazole, tetradifon, tetrafluron, tetramethrin,tetramethylfluthrin, tetramine, tetranactin, tetrasul, thallium sulfate,thenylchlor, theta-cypermethrin, thiabendazole, thiacloprid,thiadifluor, thiamethoxam, thiapronil, thiazafluron, thiazopyr,thicrofos, thicyofen, thidiazimin, thidiazuron, thiencarbazone,thiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl,thifluzamide, thiobencarb, thiocarboxime, thiochlorfenphim, thiocyclam,thiocyclam hydrochloride, thiocyclam oxalate, thiodiazole-copper,thiodicarb, thiofanox, thiofluoximate, thiohempa, thiomersal, thiometon,thionazin, thiophanate, thiophanate-methyl, thioquinox,thiosemicarbazide, thiosultap, thiosultap-diammonium,thiosultap-disodium, thiosultap-monosodium, thiotepa, thiram,thuringiensin, tiadinil, tiaojiean, tiocarbazil, tioclorim, tioxymid,tirpate, tolclofos-methyl, tolfenpyrad, tolylfluanid, tolylmercuryacetate, topramezone, tralkoxydim, tralocythrin, tralomethrin,tralopyril, transfluthrin, transpermethrin, tretamine, triacontanol,triadimefon, triadimenol, triafamone, tri-allate, triamiphos,triapenthenol, triarathene, triarimol, triasulfuron, triazamate,triazbutil, triaziflam, triazophos, triazoxide, tribenuron,tribenuron-methyl, tribufos, tributyltin oxide, tricamba, trichlamide,trichlorfon, trichlormetaphos-3, trichloronat, triclopyr,triclopyr-butotyl, triclopyr-ethyl, triclopyr-triethylammonium,tricyclazole, tridemorph, tridiphane, trietazine, trifenmorph,trifenofos, trifloxystrobin, trifloxysulfuron, trifloxysulfuron-sodium,triflumizole, triflumuron, trifluralin, triflusulfuron,triflusulfuron-methyl, trifop, trifop-methyl, trifopsime, triforine,trihydroxytriazine, trimedlure, trimethacarb, trimeturon, trinexapac,trinexapac-ethyl, triprene, tripropindan, triptolide, tritac,triticonazole, tritosulfuron, trunc-call, uniconazole, uniconazole-P,urbacide, uredepa, valerate, validamycin, valifenalate, valone,vamidothion, vangard, vaniliprole, vernolate, vinclozolin, warfarin,warfarin-potassium, warfarin-sodium, xiaochongliulin, xinjunan,xiwojunan, XMC, xylachlor, xylenols, xylylcarb, yishijing, zarilamid,zeatin, zengxiaoan, zeta-cypermethrin, zinc naphthenate, zinc phosphide,zinc thiazole, zineb, ziram, zolaprofos, zoxamide, zuomihuanglong,α-chlorohydrin, α-ecdysone, α-multistriatin, and α-naphthaleneaceticacid.
 9. The composition of claim 1, further comprising anagriculturally acceptable carrier.
 10. The composition of claim 1,wherein the pyridine triazole compound is in the form of a pesticidallyacceptable acid addition salt.
 11. The composition of claim 1, whereinthe pyridine triazole compound is in the form of a salt derivative. 12.The composition of claim 1, wherein the pyridine triazole compound is inthe form a hydrate.
 13. The composition of claim 1, wherein the pyridinetriazole compound is a resolved stereoisomer.
 14. The composition ofclaim 1, wherein the pyridine triazole compound is in the form a crystalpolymorph.
 15. The composition of claim 1, wherein the pyridine triazolecompound comprises a ²H in place of ¹H.
 16. The composition of claim 1,wherein the pyridine triazole compound comprises a ¹³C in place of a¹²C.
 17. The composition of claim 1, further comprising a biopesticide.18. The composition of claim 1, further comprising one or more of thefollowing compounds: (a)3-(4-chloro-2,6-dimethylphenyl)-4-hydroxy-8-oxa-1-azaspiro[4,5]dec-3-en-2-one;(b)3-(4′-chloro-2,4-dimethyl[1,1′-biphenyl]-3-yl)-4-hydroxy-8-oxa-1-azaspiro[4,5]dec-3-en-2-one;(c) 4-[[(6-chloro-3-pyridinyl)methyl]methylamino]-2(5H)-furanone; (d)4-[[(6-chloro-3-pyridinyl)methyl]cyclopropylamino]-2(5H)-furanone; (e)3-chloro-N2-[(1S)-1-methyl-2-(methylsulfonyl)ethyl]-N1-[2-methyl-4-[1,2,2,2-tetrafluoro-1-(trifluoromethyl)ethyl]phenyl]-1,2-benzenedicarboxamide;(f) 2-cyano-N-ethyl-4-fluoro-3-methoxy-benenesulfonamide; (g)2-cyano-N-ethyl-3-methoxy-benzenesulfonamide; (h)2-cyano-3-difluoromethoxy-N-ethyl-4-fluoro-benzenesulfonamide; (i)2-cyano-3-fluoromethoxy-N-ethyl-benzenesulfonamide; (j)2-cyano-6-fluoro-3-methoxy-N,N-dimethyl-benzenesulfonamide; (k)2-cyano-N-ethyl-6-fluoro-3-methoxy-N-methyl-benzenesulfonamide; (l)2-cyano-3-difluoromethoxy-N,N-dimethylbenzenesulfon-amide; (m)3-(difluoromethyl)-N-[2-(3,3-dimethylbutyl)phenyl]-1-methyl-1H-pyrazole-4-carboxamide;(n)N-ethyl-2,2-dimethylpropionamide-2-(2,6-dichloro-α,α,α-trifluoro-p-tolyl)hydrazone; (o)N-ethyl-2,2-dichloro-1-methylcyclopropane-carboxamide-2-(2,6-dichloro-α,α,α-trifluoro-p-tolyl)hydrazone nicotine; (p)O-{(E-)-[2-(4-chloro-phenyl)-2-cyano-1-(2-trifluoromethylphenyl)-vinyl]}S-methylthiocarbonate; (q)(E)-N1-[(2-chloro-1,3-thiazol-5-ylmethyl)]-N2-cyano-N1-methylacetamidine;(r)1-(6-chloropyridin-3-ylmethyl)-7-methyl-8-nitro-1,2,3,5,6,7-hexahydro-imidazo[1,2-a]pyridin-5-ol;(s) 4-[4-chlorophenyl-(2-butylidine-hydrazono)methyl)]phenyl mesylate;and (t)N-Ethyl-2,2-dichloro-1-methylcyclopropanecarboxamide-2-(2,6-dichloro-α,α,α-trifluoro-p-tolyl)hydrazone.19. The composition of claim 1, further comprising a compound having oneor more of the following modes of action: acetylcholinesteraseinhibitor; sodium channel modulator; chitin biosynthesis inhibitor; GABAand glutamate-gated chloride channel antagonist; GABA andglutamate-gated chloride channel agonist; acetylcholine receptoragonist; acetylcholine receptor antagonist; MET I inhibitor;Mg-stimulated ATPase inhibitor; nicotinic acetylcholine receptor; Midgutmembrane disrupter; oxidative phosphorylation disrupter, and ryanodinereceptor (RyRs).
 20. The composition of claim 1, further comprising aseed.
 21. The composition of claim 1, further comprising a seed that hasbeen genetically modified to express one or more specialized traits. 22.The composition of to claim 1, wherein the composition is encapsulatedinside, or placed on the surface of, a capsule.
 23. The composition ofclaim 1, wherein the composition is encapsulated inside, or placed onthe surface of, a capsule, wherein the capsule has a diameter of about100-900 nanometers or about 10 -900 microns.
 24. A process comprisingapplying a composition of claim 1, to an area to control a pest, in anamount sufficient to control such pest.
 25. The process of claim 24,wherein the pest is selected from beetles, earwigs, cockroaches, flies.aphids, scales, whiteflies, leafhoppers, ants, wasps, termites, moths,butterflies, lice, grasshoppers, locusts, crickets, fleas, thrips,bristletails, mites, ticks, nematodes, and symphylans.
 26. The processof claim 24, wherein the pest is from the Phyla Nematoda or Arthropoda.27. The process of claim 24, wherein the pest is from the SubphylaChelicerata, Myriapoda, or Hexapoda.
 28. The process of claim 24,wherein the pest is from the Class of Arachnida, Symphyla, or Insecta.29. The process of claim 24, wherein the pest is from the OrderAnoplura, Order Coleoptera, Order Dermaptera, Order Blattaria, OrderDiptera, Order Hemiptera, Order Hymenoptera, Order Isoptera, OrderLepidoptera, Order Mallophaga, Order Orthoptera, Order Siphonaptera,Order Thysanoptera, Order Thysanura, Order Acarina, or Order Symphyla.30. The process of claim 24, wherein the pest is MYZUPE or BEMITA. 31.The process of claim 24, wherein an amount of the composition is fromabout 0.01 grams per hectare to about 5000 grams per hectare.
 32. Theprocess of claim 24, wherein an amount of the composition is from about0.1 grams per hectare to about 500 grams per hectare.
 33. The process ofclaim 24, wherein an amount of the composition is from about 1 gram perhectare to about 50 grams per hectare.
 34. The process of claim 24,wherein the area is an area where apples, corn, cotton, soybeans,canola, wheat, rice, sorghum, barley, oats, potatoes, oranges, alfalfa,lettuce, strawberries, tomatoes, peppers, crucifers, pears, tobacco,almonds, sugar beets, or beans, are growing, or the seeds thereof aregoing to be planted.
 35. The process of claim 24, further comprisingapplying the composition to a genetically modified plant that has beengenetically modified to express one or more specialized traits.
 36. Theprocess of claim 24, where the composition further comprises ammoniumsulfate.
 37. A method of preparing a pyridine triazole compounds offormula I, comprising: reacting a pyridine triazole compounds of formula1-1 with an aryl or heterocyclic halide of formula 1-2,

wherein R₁, R₂, R₃, R₄, R₅, Z, and x are defined as in claim
 1. 38. Amethod of preparing a pyridine triazole compounds of formula I,comprising: reacting 4-iodo-triazole compounds of formula 2-1 with anaryl or heterocyclic boronic acid compounds of formula 2-2,

wherein R₁, R₂, R₃, R₄, R₅, Z, and x are defined as in claim 1.